4-Methylmorpholine → HCID 15158208, compound

A solution of 2.0 mL (15.9 mmol) of cyclopentylacetic acid in 80 mL of CH2Cl2 at 0° C. was treated with 3.7 mL (33.6 mmol) of N-methyl-morpholine and 2.2 mL (16.9 mmol) of isobutyl chloroformate. After stirring for 20 min, 1.61 g (16.5 mmol) of N,O-dimethylhydroxylamine HCl was added. The reaction was warmed to rt and stirred for 3 h. The reaction was partitioned between 200 mL of EtOAc and 200 mL 2.0 N HCl. After separating the phases, the organic layer was washed with 200 mL of 1.0 N NaHCO3, dried over Na2SO4 and concentrated. Flash chromatography on silica gel using 4:1 v/v hexanes/EtOAc afforded 2.28 g (83%) of the title compound: RF: 0.27 (4:1 v/v hexanes/EtOAc). 1H NMR (300 MHz) δ 1.12-1.23 (m, 2H), 1.51-1.89 (m, 6H), 2.28 (m, 1H), 2.44 (d, J=7.5, 2H), 3.18 (s, 3H), 3.67 (s, 3H).

1. stirringstirred for 3 h
2. customThe reaction was partitioned between 200 mL of EtOAc and 200 mL 2.0 N HCl
3. customAfter separating the phases
4. washthe organic layer was washed with 200 mL of 1.0 N NaHCO3
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-379f4ae539764e1fb1cf6027b7996754

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1