Chloroacetone → (cis)-3-(4-Methyloxazol-2-yl)cyclopentanamine hydrochloride

HRID 2404396Notes

Reaction equation

HRID 2404396 reaction equation
[C:1]([C@@H:4]1[CH2:8][CH2:7][C@H:6]([NH:9]C(=O)OC(C)(C)C)[CH2:5]1)(=[O:3])[NH2:2].[Cl:17][CH2:18][C:19](=O)[CH3:20]>CCO>[ClH:17].[CH3:20][C:19]1[N:2]=[C:1]([C@@H:4]2[CH2:8][CH2:7][C@H:6]([NH2:9])[CH2:5]2)[O:3][CH:18]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 59028693cis-3-(Boc-amino)cyclopentanecarboxamide

Product 1

HCID 68313416(cis)-3-(4-Methyloxazol-2-yl)cyclopentanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Example 120A (300 mg, 1.3 mmol) in EtOH (2 mL) was added chloroacetone (0.3 mL, 3.9 mmol). The reaction mixture was stirred at reflux for 64 hours, cooled to ambient temperature, and concentrated. Trituration of the residue in diethyl ether afforded the title compound. LC/MS (ESI+) M/Z 167 [M+H]+.

Workup

  1. temperatureat reflux for 64 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c3267e4da448dc8e717916aa26a257
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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