Dimethyl Sulfide → HCID 66848370, compound

3-Cyclopentanecarbonyl-2-oxopyrrolidine-1-carboxylic acid t-butyl ester (1.2 g, 4.4 mmol) was dissolved in THF (3.5 mL, 43.7 mmol) under nitrogen. 2M BH3.Me2S in THF (6.6 mL, 13.1 mmol) was added via syringe over 15 minutes. The mixture was stirred at room temperature for 1 hour, then heated at 65° C. for 24 hours. After an additional 48 hours, the mixture was placed on an ice bath and the reaction slowly quenched with cold MeOH (100 mL). The mixture was stirred for 15 minutes, then diluted with EtOAc (30 mL), and washed with saturated aqueous NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated by rotary evaporation to yield a yellow oil (300 mg). The oil was purified by preparative HPLC (2″ column; 5-50% MeCN/H2O; 0.1% TFA buffer; at 40 mL/min over 80 minutes). The desired fractions were collected, frozen and lyophilized to yield the title compound (939 mg). MS m/z: [M+H]+ calcd for C15H27NO3, 269.3; found 270.4.

1. temperatureheated at 65° C. for 24 hours
2. waitAfter an additional 48 hours
3. customthe mixture was placed on an ice bath
4. customthe reaction
5. customslowly quenched with cold MeOH (100 mL)
6. stirringThe mixture was stirred for 15 minutes
7. additiondiluted with EtOAc (30 mL)
8. washwashed with saturated aqueous NaHCO3 (2×50 mL)
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated by rotary evaporation

ORD record

ord-107f7b3afcca4c5b8fa005c2a7a8c768

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994209B2