Cesium carbonate → HCID 131722795, compound

Participants

Reaction Steps

A mixture of crude 2-(R/S)-(3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidin-1-yl)-(2-chlorophenyl)acetic acid (from EXAMPLE 10, Step A), 338 mg (1.0 mmol) of cesium carbonate and 0.14 mL (1.0 mmol) of 4-(methoxy)benzyl chloride in 3 mL of DMF was stirred at rt for 22 h. The reaction mixture was diluted with 100 mL of ether and washed with 100 mL of 1.0 N NaHCO3. The layers were separated and the aqueous phase was extracted with 100 mL of ether. The combined organic phases were dried over MgSO4 and concentrated. Flash chromatography using 9:1 v/v hexanes/EtOAc as the eluant afforded 377 mg (63%, two steps) of the title compound: RF: 0.68 (4:1 v/v hexanes/EtOAc). For the pair of diastereomers: 1H NMR (300 MHz) δ 0.0, 0.01, 0.02,0.04 (4s, 6H), 0.86,0.88 (2s, 9H), 2.42 (m, 1H), 2.67 (m, 1H), 2.84-3.10 (m, 4H), 3.57-3.62 (m, 2H), 3.83 (s, 31), 4.80, 4.81 (2s, 1H), 5.10 (ABq, J=12.1, 2H), 6.83-6.87 (m, 2H), 7.20-7.41 (m, 10H), 7.73 (m, 1H).

Provenance & Evidence