Dimethylformamide → (1S,3R,4R)-N-Hydroxy-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxamide

To a solution of (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (224 mg, 0.913 mmol) in dichloromethane (3.5 ml) were added oxalyl chloride (0.17 ml, 1.92 mmol) and N,N-dimethylformamide (0.07 ml, 0.913 mmol) while being cooled with ice, and the mixture was stirred at room temperature for 30 minutes. Separately, to a suspension of hydroxylamine hydrochloride (254 mg, 3.65 mmol) in tetrahydrofuran (1.0 ml)-water (0.2 ml) was added triethylamine (0.78 ml, 5.57 mmol) at 0° C., and the mixture was stirred at 0° C. for 15 minutes. To this reaction mixture was added the acid chloride solution at 0° C., and the mixture was stirred at room temperature for 14 hours. The reaction mixture, with water added thereto, was extracted with chloroform. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (1% methanol/chloroform), to give the entitled compound (126 mg, 53%).

1. temperaturewhile being cooled with ice
2. stirringthe mixture was stirred at 0° C. for 15 minutes
3. stirringthe mixture was stirred at room temperature for 14 hours
4. extractionwas extracted with chloroform
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. customThe solvent was evaporated
8. customthe residue was purified by silica gel column chromatography (1% methanol/chloroform)

ORDレコード

ord-9e9db1a2718b42b087f7639752d2d3b1

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07176217B2