tert-Butyl Formate → (3S*,4S*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

The title compound is prepared in a similar manner as described for Example 9/reaction step E, from (3S*,4S*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (10.4 g, 58.9 mmol) and Dess-Martin periodinane (25.0 g, 58.9 mmol) in CH2Cl2 (150 mL), slowly wet CH2Cl2 (1.17 mL of water in 150 mL of CH2Cl2) as colorless oil. MS: 244.2 [M+H-Boc]+. tR (HPLC, C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.46 min.

Provenance & Evidence