Methanol → HCID 70000907, compound
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:12](=[O:26])[CH2:13][N:14]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:15])[CH3:11])=[CH:6][CH:5]=1.CO>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])[N:14]([CH2:13][C:12](=[O:26])[N:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1)[CH3:11])[CH3:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Under argon 742.7 mg (32.4 mmol, 1.5 eq) lithium borhydride in 35 ml THF were added dropwise to 8 g (21.6 mmol) 4-[[(Benzyloxycarbonyl-methyl-amino)-acetyl]-methyl-amino]-benzoic acid methyl ester in 100 ml THF at RT. The suspension was stirred at RT over night, heated to 50° C. for 3.25 h, recooled to RT and 21 ml MeOH were added slowly. The solution was added to ice water, extracted with ether (3×), the combined organic layers were washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with a gradient of CH2Cl2/MeOH (100:0-99.9:0.1) yielding 3.9 g (52%) {[(4-Hydroxymethyl-phenyl)-methyl-carbamoyl]-methyl}-methyl-carbamic acid benzyl ester as yellow oil (Rf 0.4 CH2Cl2:MeOH 9:1), MS: 343 (MH+).