Tetrahydrofuran → HCID 53776264, compound

A solution of 1.30 g (4.5 mmol) of N-methoxy-N-methyl-3-(1-(t-butoxycarbonyl)piperidin-4-yl)propionamide (from EXAMPLE 188, Step A) in 25 (of THF at 0° C. was treated with 3.0 mL of 2.0 M (4-fluoro)phenylmagnesium bromide in ether and stirred cold for 1 h. The reaction was quenched with 100 mL of 0.5 N HCl and extracted with 150 mL of ether. The extract was washed with 50 mL of sat'd NaCl, dried and concentrated. The crude ketone in 10 mL of MeOH at 0° C. was treated with 110 mg (2.2 mmol) of NaBH4 and the resulting mixture was stirred cold for 30 min. The reaction was quenched with 5 mL of 1.0 N NAOH. The quenched mixture was partitioned between 100 mL of ether and 25 m of H2O and the layers were separated. The organic layer was dried; the aqueous layer was extracted with 100 mL of ether, the extract dried and the organic layers combined and concentrated. Flash chromatography on 40 g of silica gel using 3:2 v/v hexanes/ether as the eluant afforded 566 mg (37%) of the title compound.

1. customThe reaction was quenched with 100 mL of 0.5 N HCl
2. extractionextracted with 150 mL of ether
3. washThe extract was washed with 50 mL of sat'd NaCl
4. customdried
5. concentrationconcentrated
6. stirringthe resulting mixture was stirred cold for 30 min
7. customThe reaction was quenched with 5 mL of 1.0 N NAOH
8. customThe quenched mixture was partitioned between 100 mL of ether and 25 m of H2O
9. customthe layers were separated
10. customThe organic layer was dried
11. extractionthe aqueous layer was extracted with 100 mL of ether
12. customthe extract dried
13. concentrationconcentrated

ORD record

ord-45e96ddd6f8b4ff887b6de5d84095904

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1