Trimethylsilyldiazomethane → methyl (1S,2R)-2-aminocyclopentane-1-carboxylate hydrochloride

HRID 731313Notes

Reaction equation

HRID 731313 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[C:8]([OH:10])=[O:9].[CH3:11][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1.CO>[ClH:1].[CH3:11][O:9][C:8]([C@H:4]1[CH2:5][CH2:6][CH2:7][C@H:3]1[NH2:2])=[O:10]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 13831733(1S,2R)-(+)-2-Amino-1-cyclopentanecarboxylic acid hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(1S,2R)-2-Amino-cyclopentanecarboxylic acid hydrochloride (126 mg, 0.76 mmol) was dissolved in a 1:1 mixture of benzene and methanol (8 mL). The mixture was cooled to 0° C. A 2.0 M solution of (trimethylsilyl)diazomethane in hexanes (0.57 mL, 1.14 mmol) was added and the reaction was stirred at 25° C. for 30 min. The mixture was concentrated and dried in vacuo. The crude product was directly used in the next step.

Workup

  1. concentrationThe mixture was concentrated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-85501e515521455cb2fb6c77f51a3200
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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