(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → Hydrochloric Acid

HRID 2425426Notes

Reaction equation

HRID 2425426 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([Br:28])=[CH:20][N:21]=[C:22]([Cl:27])[C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=O)(C)(C)C.C(OC([NH:36][C@@H]1CCNC1)=O)(C)(C)C.C(OC(N([C@H]1CCNC1)C)=O)(C)(C)C>>[NH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([Br:28])=[CH:20][N:21]=[C:22]([NH2:36])[C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1.[ClH:27]

Participants

5

Reactant 3

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 7171888(S)-Methyl-pyrrolidin-3-yl-carbamic acid tert-butyl esterHCID 86627811(R)-3-(tert-Butoxycarbonylamino)-1-(1-chloro-4-bromo-5-isoquinolinesulfonyl)pyrrolidine

Product 2

HCID 313Hydrochloric AcidHCID 67243451(R)-3-Amino-1-(1-amino-4-bromo-5-isoquinolinesulfonyl)pyrrolidine

Procedure

(R)-3-(tert-Butoxycarbonylamino)-1-(1-chloro-4-bromo-5-isoquinolinesulfonyl)pyrrolidine can be prepared by using (R)-3-(tert-butoxycarbonylamino)pyrrolidine in the method of Example 35-1, Step A instead of (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine, and then the protective group of the obtained compound can be removed according to the method described in Example 39-1, Step B to obtain the title compound as hydrochloride.

Workup

  1. customthe protective group of the obtained compound can be removed

Sources & evidence

ORD record
ord-117718ca42764f8a8657619fa5d2184c
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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