Hydrochloric Acid → (2S)-2-amino-1-methyl-cyclopentanol hydrochloride

HRID 245056Notes

Reaction equation

HRID 245056 reaction equation
[OH:1][C:2]1([CH3:15])[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7]C(=O)OC(C)(C)C.[ClH:16].O1CCOCC1>ClCCl>[ClH:16].[NH2:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C:2]1([CH3:15])[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86693771tert-butyl N-[(1S)-2-hydroxy-2-methyl-cyclopentyl]carbamate

Product 1

HCID 86693769(2S)-2-amino-1-methyl-cyclopentanol hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[(1S)-2-hydroxy-2-methyl-cyclopentyl]carbamate (mixture of cis and trans diastereomers) (6.66 g, 30.9 mmol), 4 M HCl in dioxane (46.4 mL, 185.6 mmol), and dichloromethane (62 mL) is stirred at room temperature for 1 h. The reaction is concentrated in vacuo, and then redissolved in MeOH and reconcentrated to give the title compound as a brown oil (5.09 g). LC-ES/MS m/z 116 (M+1).

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. dissolutionredissolved in MeOH

Sources & evidence

ORD record
ord-ee70b90ae52a4d92b7d86dda542b8a3e
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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