3-Tert-butoxycarbonylamino-3-cyclobutyl-propionic acid → tert-butyl N-(1-cyclobutyl-3-hydroxypropyl)carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:14]1[CH2:17][CH2:16][CH2:15]1)[CH2:10][C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH:14]1[CH2:15][CH2:16][CH2:17]1)[CH2:10][CH2:11][OH:12])([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-tert-butoxycarbonylamino-3-cyclobutyl-propionic acid (0.300 g, 1.23 mmol) in THF (12 mL) was added BH3—SMe2 (1.70 mL, 3.33 mmol; 2.0 M solution in THF) at 0° C. After stirring at rt for 10 h, the reaction mixture was quenched with satd. NaHCO3, extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated in vacuo to afford (1-cyclobutyl-3-hydroxy-propyl)-carbamic acid tert-butyl ester (0.100 g); LC-MS [M+H]+ 230.0. The product is sufficiently pure for the next step and used for the next step without further purification.