tert-butyl N-(pyrrolidin-3-yl)carbamate → Hydrochloric Acid

HRID 2425383Notes

Reaction equation

HRID 2425383 reaction equation
CC1C2C(S([Cl:15])(=O)=O)=CC=CC=2C=NC=1.BrC1C2C(S(Cl)(=O)=O)=CC=CC=2C=NC=1.C(OC(NC1CCNC1)=O)(C)(C)C.C(OC([NH:51][CH:52]1[CH2:56][CH2:55][N:54]([S:57]([C:60]2[C:61]3[C:62]([CH3:70])=[CH:63][N:64]=[CH:65][C:66]=3[CH:67]=[CH:68][CH:69]=2)(=[O:59])=[O:58])[CH2:53]1)=O)(C)(C)C>>[NH2:51][CH:52]1[CH2:56][CH2:55][N:54]([S:57]([C:60]2[C:61]3[C:62]([CH3:70])=[CH:63][N:64]=[CH:65][C:66]=3[CH:67]=[CH:68][CH:69]=2)(=[O:59])=[O:58])[CH2:53]1.[ClH:15]

Participants

6

Reactant 4

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 145800584-Bromo-5-isoquinolinesulfonyl chlorideHCID 154871104-Methylisoquinoline-5-sulfonyl chlorideHCID 67245257(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-methyl-5-isoquinolinesulfonyl)pyrrolidine2×

Product 2

HCID 313Hydrochloric AcidHCID 57938944(r/s)-3-Amino-1-(4-methyl-5-isoquinolinesulfonyl)pyrrolidine

Procedure

By using 4-methyl-5-isoquinolinesulfonyl chloride obtained according to the method described in WO09728130 instead of 4-bromo-5-isoquinolinesulfonyl chloride, and 3-(tert-butoxycarbonylamino)pyrrolidine instead of (S)-3-(tert-butoxycarbonylamino)pyrrolidine in the method of Example 1-1, (R/S)-3-(tert-butoxycarbonylamino)-1-(4-methyl-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 5) can be prepared, and then the protective group of Intermediate 5 can be removed according to the method described in Example 1-1, Step B to obtain the title compound as hydrochloride.

Workup

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

Sources & evidence

ORD record
ord-ddb0fed180404df3814f88bb369ea17d
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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