Acetyl chloride → (1S,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride

HRID 905972Notes

Reaction equation

HRID 905972 reaction equation
C([Cl:4])(=O)C.[CH3:5][O:6][C:7]([C@H:9]1[CH2:13][CH2:12][C@H:11]([NH:14]C(OC(C)(C)C)=O)[CH2:10]1)=[O:8]>CO>[ClH:4].[CH3:5][O:6][C:7]([C@H:9]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2734531ST50825900

Product 1

HCID 66933221(1S,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (3.5 mL, 49.3 mmol) was added dropwise at 0° C. to 100 mL of MeOH. The resulting mixture was stirred at 0° C. for 5 minutes before adding (1S,3S)-3-tert-butoxycarbonylamino-cyclopentanecarboxylic acid methyl ester (1.192 g, 5.2 mmol). The reaction mixture was allowed to warm up to RT and stirred for 48 h before being evaporated to give crude (1S,3S)-3-amino-cyclopentanecarboxylic acid methyl ester hydrochloride which was used as is in the following step.

Workup

  1. temperatureto warm up to RT
  2. stirringstirred for 48 h
  3. custombefore being evaporated

Sources & evidence

ORD record
ord-d0e4597c60774248a40955825ca9517d
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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