Benzoyl chloride → HCID 9920605, compound

HRID 1646412Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)Cl>[C:14]([N:1]1[CH2:5][CH2:4][CH:3]([OH:6])[CH2:2]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (R)-3 hydroxy 4-(p-toluenesulfonyloxy)butylamine hydrochloride (8.8 g) in methanol 90 ml), sodium carbonate (3.3 g) was added and the mixture was stirred at room temperature for 8 hours. Then, the mixture was filtered, and the filtrate was evaporated under reduced pressure to obtain crude 3 pyrrolidinol. One tenth of the crude 3-pyrrolidinol was dissolved in methylene chloride. To the solution, triethylamine (432 μl ) was added, and after cooling to 0° C., benzoyl chloride (360 μl ) was added. After stirring for 2 hours, the mixture was evaporated under reduced pressure and purified by silica gel column chromatography (Wako Gel C200, an eluent: ethyl acetate/methanol (volume ratio of 95/5) to obtain pure N-benzoyl-3-pyrrolidinol (438 mg). Yield, 85 %.

Workup

customthe mixture was evaporated under reduced pressure
custompurified by silica gel column chromatography (Wako Gel C200

Sources & evidence

ORD record: ord-a407ab10131647eda2076e0cf3116af5
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05179212

Reaction notes

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