HCID 178471800, compound → HCID 178471796, compound
Reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13](O)=[O:14])[CH2:9][CH2:8]1)=[O:5])[CH3:2]>C1COCC1>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][OH:14])[CH2:9][CH2:8]1)[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of trans-4-ethoxycarbonylmethyl-cyclohexanecarboxylic acid (1 mmol; 214 mg) in THF (3 mL) is added 1.0 M THF solution of borane THF complex (2 mmol; 2 mL) at 0° C. under nitrogen. The solution is stirred for 1.5 hours at room temperature, quenched by dropwise addition of 1 mL of MeOH. The mixture after concentration is diluted with dichloromethane and saturated aqueous ammonium chloride solution. The product is extracted with 100 ml of dichloromethane. The organic layer after dried is separated, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane/EtOAc) to give trans-(4-hydroxymethylcyclohexyl)-acetic acid ethyl ester (166 mg, 83%); ESI-MS m/z: 201 [M++1], Retention time 1.67 min (condition A).