methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate → methyl (1S,2R)-2-aminocyclopentane-1-carboxylate hydrochloride

HRID 1662038Notes

Reaction equation

HRID 1662038 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]([O:16][CH3:17])=[O:15])=O)(C)(C)C.[ClH:18].C(OCC)(=O)C>C(OCC)(=O)C>[ClH:18].[NH2:8][C@@H:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 11322482methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 14698816methyl (1S,2R)-2-aminocyclopentane-1-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl (1S,2R)-2-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylate (0.84 g) and ethyl acetate (2.5 ml) was added a 4 M hydrogen chloride/ethyl acetate solution (5.0 ml) under ice-cooling, followed by stirring at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure to obtain methyl (1S,2R)-2-aminocyclopentanecarboxylate hydrochloride (0.72 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0f6e303c9e86432cbf16bfaff76d4751
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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