Benzoyl chloride → (S)-3-benzoyloxy-1-t-butoxycarbonylpyrrolidine

To a solution of (3S)-pyrrolidin-3-ol (0.87 g, 10.0 mmol) in THF (20 mL) was slowly added a solution of di-tert-butyl dicarbonate (2.18 g, 10.0 mmol) in THF (10 mL) at room temperature. After addition was completed, the reaction mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (0-2.5% methanol in dichloromethane) to give intermediate tert-Butyl(3S)-3-hydroxypyrrolidine-1-carboxylate. To a solution of tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (900 mg, 4.8 mmol) in CH2Cl2 (6 mL) was added Et3N (699 mg, 6.91 mmol) followed by benzoyl chloride (809 mg, 5.76 mmol) at 0° C. After addition was completed, the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between CH2Cl2 and H2O. The organic layer was successively washed with aqueous NaHCO3 and water, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (0-1% methanol in dichloromethane) to give the subtitled compound (642 mg).

1. additionAfter addition
2. customThe reaction mixture was partitioned between CH2Cl2 and H2O
3. washThe organic layer was successively washed with aqueous NaHCO3 and water
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by silica gel flash chromatography (0-1% methanol in dichloromethane)

ORD record

ord-f64d354476d34a82bdf6018f7941d0d9

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07449475B2