tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate → Hydrochloric Acid

HRID 2425404

Reaction equation

HRID 2425404 reaction equation
[Cl:1][C:2]1[C:11]2[C:10]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[N:4][CH:3]=1.[C:16]([O:20][C:21]([N:23]([C@@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1)[CH3:24])=[O:22])([CH3:19])([CH3:18])[CH3:17].BrC1C2C(S([Cl:44])(=O)=O)=CC=CC=2C=NC=1.C(O[C:50]([N:52]([C@H:54]1[CH2:58][CH2:57][NH:56][CH2:55]1)C)=O)(C)(C)C>>[C:16]([O:20][C:21]([N:23]([C@@H:25]1[CH2:29][CH2:28][N:27]([S:12]([C:10]2[C:11]3[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=3[CH:7]=[CH:8][CH:9]=2)(=[O:14])=[O:13])[CH2:26]1)[CH3:24])=[O:22])([CH3:19])([CH3:17])[CH3:18].[Cl:1][C:2]1[C:11]2[C:10]([S:12]([N:56]3[CH2:57][CH2:58][C@@H:54]([NH:52][CH3:50])[CH2:55]3)(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:5]=[N:4][CH:3]=1.[ClH:44]

Participants

7

Reactant 4

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamateHCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 145800584-Bromo-5-isoquinolinesulfonyl chlorideHCID 221219084-Chloroisoquinoline-5-sulfonyl chloride

Product 3

HCID 313Hydrochloric AcidHCID 67243985(R)-1-(4-chloro-5-isoquinolinesulfonyl)-3-(methylamino)pyrrolidineHCID 67245481(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(4-chloro-5-isoquinolinesulfonyl)pyrrolidine

Procedure

(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(4-chloro-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 21b) was prepared by using 4-chloro-5-isoquinolinesulfonyl chloride and (R)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine in the method of Example 1-3, Step A instead of 4-bromo-5-isoquinolinesulfonyl chloride and (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine, respectively, and then used in the method of Example 1-3, Step B in a similar manner to obtain the title compound as hydrochloride.

Sources & evidence

ORD record
ord-b2447040899a499e9fe17198f3eac801
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Linked notes

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