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

HRID 1962430Notes

Reaction equation

HRID 1962430 reaction equation
CC1C2C(S([Cl:15])(=O)=O)=CC=CC=2C=NC=1.C(OC(N[C@@H]1CCNC1)=O)(C)(C)C.C(OC([NH:36][C@@H:37]1[CH2:41][CH2:40][N:39]([S:42]([C:45]2[C:46]3[C:47]([CH3:55])=[CH:48][N:49]=[CH:50][C:51]=3[CH:52]=[CH:53][CH:54]=2)(=[O:44])=[O:43])[CH2:38]1)=O)(C)(C)C>>[NH2:36][C@@H:37]1[CH2:41][CH2:40][N:39]([S:42]([C:45]2[C:46]3[C:47]([CH3:55])=[CH:48][N:49]=[CH:50][C:51]=3[CH:52]=[CH:53][CH:54]=2)(=[O:44])=[O:43])[CH2:38]1.[ClH:15]

Participants

5

Reactant 3

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 154871104-Methylisoquinoline-5-sulfonyl chlorideHCID 67245848HCID 67245848, compound2×

Product 2

HCID 313Hydrochloric AcidHCID 67243342HCID 67243342, compound

Procedure

By using 4-methyl-5-isoquinolinesulfonyl chloride instead of 4-bromo-5-isoquinolinesulfonyl chloride, and (R)-3-(tert-butoxycarbonylamino)pyrrolidine instead of (S)-3-(tert-butoxycarbonylamino)pyrrolidine in the method of Example 1-1, (R)-3-(tert-butoxycarbonylamino)-1-(4-methyl-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 513) can be prepared, and then the protective group of Intermediate 5b can be removed according to the method described in Example 1-1, Step B to obtain the title compound as hydrochloride.

Workup

  1. customcan be prepared
  2. customthe protective group of Intermediate 5b can be removed

Sources & evidence

ORD record
ord-d4358613a77d4b368eaf81c54aceaab7
Source dataset
uspto-grants-2013_04
Patent number
US08415372B2

Reaction notes

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