Sodium bis(trimethylsilyl)amide → HCID 76477614, compound

A solution of 450 mg (1.81 mmol) of cyclopentylacetic acid, 4-(methoxy)benzyl ester (from EXAMPLE 15, Step A) in 6 mL of THF was added to 2.15 mL of 1.0 M sodium bis(trimethylsilyl)amide solution in THF at −78° C. and the resulting mixture was stirred cold for 15 min. A solution of 700 mg (2.67 mmol) of (benzenesulfonyl)phenyloxaziridine in 3 mL of THF was the added and the resulting mixture was stirred at −78° C. for 1 h. The reaction was quenched with sat'd NH4Cl and warmed to rt. The mixture was concentrated and the residue was dissolved in 100 mL of ether and washed with 100 mL of sat'd NaCl. The phases were separated and the aqueous layer was extracted with 100 mL of ether. The combined organic layers were dried over MgSO4 and concentrated. Flash chromatography on silica gel using 9:1 v/v hexanes/EtOAc as the eluant afforded 233 mg (48%) of the title compound: RF: 0.37 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.36-1.69 (m, 8H), 2.22 (m, 11H), 3.81 (s, 3H), 4.14 (d, J=4.9, 11H), 5.14 (ABq, J=11.8, 2H), 6.89 (d, J=8.8, 2H), 7.29 (d, J=8.8, 2H).

1. additionadded
2. stirringthe resulting mixture was stirred at −78° C. for 1 h
3. customThe reaction was quenched with sat'd NH4Cl
4. concentrationThe mixture was concentrated
5. dissolutionthe residue was dissolved in 100 mL of ether
6. washwashed with 100 mL of sat'd NaCl
7. customThe phases were separated
8. extractionthe aqueous layer was extracted with 100 mL of ether
9. dry with materialThe combined organic layers were dried over MgSO4
10. concentrationconcentrated

ORD record

ord-bca92db97c76495fbce48eec229926de

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1