Sodium triacetoxyborohydride → 2-(4-Chloro-benzylamino)-cyclopentanecarboxylic acid ethyl ester

HRID 731383Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)=[O:5])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

2-(4-Chloro-benzylamino)-cyclopent-1-enecarboxylic acid ethyl ester (2.98 g, 10.68 mmol) was dissolved in glacial acetic acid (20 mL) and sodium triacetoxyborohydride (6.79 g, 32.04 mmol) was added at 0° C. The solution was allowed to warm to 25° C. and stirred for 3 h. The acetic acid was removed in vacuo and the residue was dissolved in dichloromethane. The solution was washed with saturated aqueous sodium bicarbonate solution followed by saturated aqueous brine solution. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the desired product, 2-(4-chloro-benzylamino)-cyclopentanecarboxylic acid ethyl ester (2.43 g, 8.64 mmol, 80.9%), as a yellow oil. LC-MS (ESI) calcd for C15H20ClNO2 281.12, found 282.0 [M+H+].

Workup

customThe acetic acid was removed in vacuo
dissolutionthe residue was dissolved in dichloromethane
washThe solution was washed with saturated aqueous sodium bicarbonate solution
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-16e3c999102349b7b6b843633b8aaf1f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582626B2

Reaction notes

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