tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate → trans-3-methoxy-4-hydroxy-1-Boc-Pyrrolidine
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O-:15].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@@H:10]([O:15][CH3:14])[C@H:12]([OH:11])[CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3 g, 16 mmol) was dissolved in 2-Me-THF (10 mL) and a solution of sodium methoxide in methanol (10 mL of a 25% solution) was added and the reaction stirred at rt overnight. Reaction was quenched with sat. NH4Cl and concentrated, then after extraction with EtOAc, residue was purified by column chromatography on SiO2 (35% EtOAc/heptane) which gave the title compound IIa as a clear oil (1.05 g).