Trifluoroacetic acid → HCID 66982187, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-oxo-3-((trimethylstannyl)methyl)pyrrolidine-1-carboxylate (D30) (3.1 g, 6.86 mmol) in THF (200 ml) cooled at −78° C., LiEt3BH 1M sol in THF (17.2 ml) was added dropwise. The reaction was left at −78° C. for 2 hrs then water (50 ml) and the reaction extracted with Et2O (3×100 ml). The organic phases were combined, dried over Na2SO4 and evaporated in vacuo to afford a residue which was dissolved in DCM (120 ml) and cooled at 0° C. TFA (1.31 ml, 17.2 mmol) was added and the reaction was stirred 10 min at this temperature. K2CO3 sat sol (100 ml) was added and the mixture extracted with DCM (3×100 ml). The organic phases were collected, dried over Na2SO4 and evaporated in vacuo to afford a residue which was purified by BiotageSNAP-Si column (50 g) eluting with a mixture cHex/EtOAc 95/5. Collected fractions after solvent evaporation afforded the title compound (D31) (2.1 g).

Provenance & Evidence