Toluene → Methyl 1-aminocyclopentaneacetate

HRID 1172390Notes

Reaction equation

HRID 1172390 reaction equation
Cl.[NH2:2][C:3]1([CH2:8][C:9]([OH:11])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:12][Si](C=[N+]=[N-])(C)C.C1(C)C=CC=CC=1>CO.C1C=CC=CC=1>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:3]1([NH2:2])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 162124922-(1-Aminocyclopentyl)acetic acid hydrochloride

Product 1

HCID 57446164Methyl 1-aminocyclopentaneacetateYield 98%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of (1-amino-cyclopentyl)-acetic acid hydrochloride (363 mg, 2.02 mmol) in a 1:1 mixture of anhydrous methanol/benzene (20 mL) cooled to 0° C. under a nitrogen environment was treated dropwise via syringe with a 2.0 M solution of trimethylsilyldiazomethane in toluene (2.0 mL, 4.0 mmol). The reaction mixture was allowed to warm to 25° C., stirred for 1 h, and concentrated in vacuo to give (1-amino-cyclopentyl)-acetic acid methyl ester (311 mg, 98%) as a colorless oil. LC-MS (ESI) calculated for C8H15FNO2: 157.2, found 158.2 [M+H+].

Workup

  1. temperatureto warm to 25° C.
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b12564071eb34004850b76cdbc7c4cca
Source dataset
uspto-grants-2010_11
Patent number
US07834009B2

Reaction notes

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