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

HRID 2425406Notes

Reaction equation

HRID 2425406 reaction equation
C(O[C:6]([N:8]([C@@H:10]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[C:19]3[C:20]([F:28])=[CH:21][N:22]=[CH:23][C:24]=3[CH:25]=[CH:26][CH:27]=2)(=[O:17])=[O:16])[CH2:11]1)C)=O)(C)(C)C.FC1C2C(S([Cl:43])(=O)=O)=CC=CC=2C=NC=1.C(OC(N([C@@H]1CCNC1)C)=O)(C)(C)C.BrC1C2C(S(Cl)(=O)=O)=CC=CC=2C=NC=1.C(OC(N([C@H]1CCNC1)C)=O)(C)(C)C>>[F:28][C:20]1[C:19]2[C:18]([S:15]([N:12]3[CH2:13][CH2:14][C@@H:10]([NH:8][CH3:6])[CH2:11]3)(=[O:16])=[O:17])=[CH:27][CH:26]=[CH:25][C:24]=2[CH:23]=[N:22][CH:21]=1.[ClH:43]

Participants

7

Reactant 5

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamateHCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 118565474-Fluoroisoquinoline-5-sulfonylchlorideHCID 145800584-Bromo-5-isoquinolinesulfonyl chlorideHCID 67243108(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(4-fluoro-5-isoquinolinesulfonyl)pyrrolidine2×

Product 2

HCID 313Hydrochloric AcidHCID 67243602(R)-1-(4-Fluoro-5-isoquinolinesulfonyl)-3-(methylamino)pyrrolidine

Procedure

(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(4-fluoro-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 22b) can be prepared by using 4-fluoro-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-0d58b2e5889249dca4fb8a84a3d3cbe2
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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