Ethyl formate → HCID 59468952, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(1,1-dimethylethyl) 2-methyl (2S,5R)-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-1,2-pyrrolidinedicarboxylate (D58, 0.35 g, 0.76 mmol) in dry THF (6 ml) at −78° C. was added dropwise LiHMDS (0.80 ml, 0.80 mmol, 1M solution in THF). The mixture was allowed to warm to −40° C. and was stirred for 40 min at that temperature. Then the mixture was again cooled to −78° C. and ethyl formate (1.23 ml, 15.2 mmol) was added. The mixture was left stirring for another 8 h at the same temperature. The reaction was quenched with brine, diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated. The crude material was dissolved in MeOH (5 ml) at 0° C. and NaBH4 (30 mg, 0.79 mmol) was added. The mixture was stirred for 1 h at the same temperature. The reaction was quenched with a 5% solution of aqueous NaHCO3, diluted with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by chromatography on silica gel using cyclohexane and ethyl acetate (9:1 to 75:25) to afford the title compound as a colourless oil (170 mg, 46%); Rt (HPLC): 5.78 min; MS: (ES/+) m/z: 512 [M+Na] C26H32FNO7 requires 489.

Provenance & Evidence