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Page 1 of 11
`
`Grunenthal GmbH Exhibit 2030
`Rosellini v. Grunenthal GmbH
`IPR2016-00471
`
`

`
`Class
`
`Reactants Bu351, HBr-Salz
`
`Bromwasserstoffséure, 47%-ig in Wasser
`
`NatriumhydrogencalbonabL6sung, gesiittigt in Wasser nla
`
`150.00 100.00 871.32
`E.0
`
`nla
`
`Actual Amounts
`
`Properties
`
`Volume
`
`I‘
`
`Strength
`JF
`
`15.81
`
`3.16 M
`
`no\3 r-
`
`nla
`
`1.00
`
`1.50
`
`1.00
`
`1.32
`
`0.81
`
`0.86
`
`1.00
`
`316.28
`
`80.91
`
`84.01
`
`84.93
`
`72.11
`
`108.64
`
`18.02
`
`8.71 M
`
`15.60M
`
`11.17 M
`
`7.91 M
`
`55.51 M
`
`132.50 100.00 1560.07
`:E
`3F
`
`==\\\sna9:
`
`nla
`
`nla
`
`nla
`
`D
`
`H
`
`Chemicals
`
`Dich|ormethan,Kannenware
`
`Methylethylketon, Kannenware
`
`Trimethylchlorsilan
`
`Wasser, deion.
`
`Products
`
`PG1026
`
`nla
`
`10.09
`
`100.00 wt/wt%
`
`1.00
`
`257.80
`
`Identity
`
`Theoretical Yield (corrected for
`product strength)
`
`Actual Yield
`
`Process Mass
`Intensity Review
`
`Meta
`Data
`
`257.80 (calculated)
`
`PG1026,C14H24C|N0,
`
`1.00equiv; 15.81mmoles;4.08
`
`g (Based on Planned)
`1.00 equiv; 15.81 mmoles; 4.08
`g (Based on Actuals)
`
`Patentvorschrift EP 0 693 475 B1:
`
`[Image 1]
`
`0.64 equiv; 10.09 mmoles; 2.60 Theoretical)
`g (Based on Actuals)
`110.58 (Based on
`Actuals)
`
`74.37(Basedon I
`
`63.80%
`
`(+)-(1R.2R)-3-(3-Dirnethylamino-1-aihyl-2methyl-propyI)phenoI, Hydrochlorid (+21)
`4.3 9 (15 mmol) (+23) aus Sims 2 wurden mit 100 ml konzentruene: Bromwasserstoflsauro varsgtzt. Anschligflgnd
`yvurde zwen Stunden unlef Flfickllufi erhdzl. Nach dem Abkflhlan aul Raurntamperatur wurde aas Fleaktnonsgemisch
`Im Wasserstrah Ivakuum enngeengl. Der Fifickstand wurda bis zur alkaluschen Fqeaumon mu konzenme.-(er Namumhy.
`drogencarbonatlésung verseut. Nach zweirnaluger Extraknon mit ye 50 ml Dichlovmalhan wurden due vereiniglen or-
`ganiachn Phasen fiber Nalriumsulfat getrocknel. Anschliooond wurde Dlchlorrnathan im Vakuum abdesulliert und dar
`Rflchstand (4 g)Ain 2-Butanon aulgenommen. Nach cler Zugabe von Trimemylchlorsnlan/Wasser kristallisierten 3.8 g
`(98 9!: car Theone) Hydrochlond (+21) aus.
`Schmp 194 496°C
`|u]D“7 = + 24.5’ (c = 1 .10; Methanol)
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00055549
`
`Page 2 of 11
`
`

`
`12. Nov. 09
`
`* 4,3g Bu351-HCI-Salz entsprechen 5,0g Bu351-HBr-Salz
`
`Apparatur: 250m|—Rundko|ben, Magnetruhrer, (")|bad, Ruckflufskuhler
`
`Ausfiihrung:
`— das Olbad auf 130°C vorheizen
`— Bu351, HBr—Sa|z (5 g [Limiting Reagent]; 1.00 equiv; 15.81 mmoles; 5.00 mL; 5.00 g; [Actua|]) mit Bromwasserstoffséiure, 47%—ig in Wasser (100 mL;
`871.32 mmoles; 100.00 mL; 150.00 g; [Actua|]) versetzen
`— unter Riihren 2 Stunden refluxieren
`
`Aufarbeitung:
`— das ("blbad entfernen und etwas abkuhlen lassen
`— am Rotationsverdampfer einengen
`— den Ruckstand in einen 500m|—Er|enmeyer umfullen und langsam (Vorsicht: heftige Gasentwicklung) mit geséittigter Natriumhydrogencarbonat—L6sung
`alkalisieren (pH9)
`- zweimal mit insgesamt Dichlormethan, Kannenware (100 mL; 1.56 moles; 100.00 mL; 132.50 g; [Actua|]) extrahieren
`— den organischen Extrakt Uber Natriumsulfat filtrieren, einengen und im Vakuum trocknen = 2,603g Base
`
`Hydrochlorid-Féllung:
`- 2,603g Base (entsprechen 11,75mmo|) in 17,5m| MEK aufnehmen
`— unter Ruhren 0,235m| Wasser zugeben
`- 1,49m| (entsprechen 11,75mmo|) Trimethylchlorsilan zugeben
`— 90 Minuten im Eisbad nachruhren
`- vom Feststoff absaugen; diesen mit MEK nachwaschen und trockensaugen = 2,60g Hydrochlorid (cremefarbener Feststoff)
`
`Pulverdiffraktometrie:
`
`PG1026—001—1—1, Hydrochlorid: Polymorph B
`
`theor. Ausbeute:
`Ausbeute:
`Aussehen:
`Fp:
`
`4,08g Hydrochlorid
`PG1026 (2.6 g; 0.64 equiv; 10.09 mmoles; 2.60 g; 63.80% yield; [Actua|])
`cremefarbener Feststoff
`199-201 °C
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00055550
`
`Page 3 of 11
`
`

`
`Characterization of Dichlormethan, Kannenware
`
`Material Data
`
`EEDED ZIZZ
`
`Chart Data
`
`fifle Methylene Chloride
`
`Number of Points
`
`32
`
`Observed Frequency
`
` NIST Standard Reference Data
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00056651
`
`Page 4 of 11
`
`

`
`UJ
`
`U EC
`
`:22
`
`|
`
`20
`
`an
`
`HIGHLY CONFIDENTIAL
`
`?D
`
`an
`
`GRT-NUC00056652
`
`2%
`
`E L
`
`‘:_|
`LIJ
`III:
`
`Page 5 of 11
`
`

`
`Characterization of Dichlormethan, Kannenware
`
`Material Data
`
`-a
`
`Em
`
`°"v°' @
`
`@ —
`
`:a
`-m
`—:n
`
`E S
`
`olubility 50.67 g/100-mL
`
`Chart Data
`
`Methylene Chloride
`88°
`
`Sadtler Research Labs Under US—EPA Contract
`
` NIST Standard Reference Data Program
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00055553
`
`Page 6 of 11
`
`

`
`1nnn
`
`HIGHLY CONFIDENTIAL
`
`snnn
`
`GRT-NUC00056654
`
`LIJ
`L3
`
`EIII
`II
`
`DL
`
`I".|
`
`E
`
`Page 7 of 11
`
`

`
`Characterization of Methylethylketon, Kannenware
`
`Material Data
`
`EEwE@ ZIZZ
`
`Title
`
`2—Butanone
`
`Observed Frequency
`
` NIST Standard Reference Data
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00056655
`
`Page 8 of 11
`
`

`
`UJ
`
`U EC
`
`:22
`
`|
`
`2::
`
`3::
`
`HIGHLY CONFIDENTIAL
`
`an
`
`GRT-NUC00056655
`
`2%
`
`E L
`
`‘:_|
`LIJ
`III:
`
`Page 9 of 11
`
`

`
`Characterization of Methylethylketon, Kannenware
`
`Material Data
`
`EEm
`
`\E/\ %
`
`@ ZIEm
`
`79-6 “C
`Solubility 60.65 g/100-mL
`
`Chart Data
`
`2—Butanone
`88°
`
`Sadtler Research Labs Under US—EPA Contract
`
` NIST Standard Reference Data Program
`
`HIGHLY CONFIDENTIAL
`
`GRT-NUC00055557
`
`Page 10 of 11
`
`

`
`1nnn
`
`HIGHLY CONFIDENTIAL
`
`snnn
`
`GRT-NUC00056658
`
`LIJ
`L3
`
`EIII
`II
`
`DL
`
`I".|
`
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`
`Page 11 of 11

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