Hydrochloric Acid → HCID 67258391, compound

HRID 2421504Notes

Reaction equation

HRID 2421504 reaction equation
C[O:2]C([C@@]1(N)CC[C@H](C2C=CC(Br)=CC=2)C1)=O.[ClH:18].[CH3:19][O:20][C:21]([C@:23]1([NH2:35])[CH2:27][CH2:26][C@H:25]([C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)[CH2:24]1)=[O:22]>>[OH2:2].[ClH:18].[NH2:35][C@:23]1([C:21]([O:20][CH3:19])=[O:22])[CH2:27][CH2:26][C@H:25]([C:28]2[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=2)[CH2:24]1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 24997352HCID 24997352, compoundHCID 44191917Methyl (1S,3S)-1-amino-3-(4-bromophenyl)cyclopentanecarboxylate

Product 1

HCID 67258391HCID 67258391, compoundYield 36%

Procedure

The crude mixture of (1R,3S)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid methyl ester; hydrochloride and (1S,3S)-1-amino-3-(4-bromo-phenyl)-cyclopentanecarboxylic acid methyl ester; hydrochloride (from General Procedure F) (approx. 2.6 mol) was combined with 15 L of aqueous 1,2-DME solution (4.8% water content). The slurry was mixed for 3 h at 50° C., allowed to cool to room temperature and mixed at room temperature for 15 h. The resulting mixture is filtered and dried in vacuo at 60° C. to provide (1R,3S)-methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate hydrochloride hydrate as a white solid (332 g, 36% yield). Chiral HPLC (Table 1, Method b). Rt=19.9 min., LCMS (Table 1, Method a) Rt=1.80 min (ELSD); m/z: 198 (M+H)+.

Workup

  1. additionThe slurry was mixed for 3 h at 50° C.
  2. additionmixed at room temperature for 15 h
  3. filtrationThe resulting mixture is filtered
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-748a91bf5a9b49c4a63c034c21eef95f
Source dataset
uspto-grants-2011_06
Patent number
US07956195B2

Reaction notes

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