Benzoyl chloride → 1-Benzoyl-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323403Notes

Reaction equation

[C:1]([C@](C(O)=O)(O)[C@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][CH:3]=1.[C:31]1([C:37]2([CH2:42][CH2:43][OH:44])[CH2:41][CH2:40][NH:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C.CCCCCC.C(=O)(O)[O-].[Na+].C(Cl)(=O)C1C=CC=CC=1>CC(C)=O.ClCCl.CO>[C:1]([N:39]1[CH2:40][CH2:41][C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([CH2:42][CH2:43][OH:44])[CH2:38]1)(=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Combine (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (11.1 g, 18.3 mmol) and acetone/water (1/1, 200 mL). Cool to about 0° C. in an ice bath and add sodium bicarbonate (10.6 g, 217.6 mmol). Warm to ambient temperature and slowly add a solution of benzoyl chloride (4.2 g, 365 mmol) in acetone (10 mL). After 18 hours, filter and dilute the filtrate with ethyl acetate. Extract the diluted filtrate with a saturated aqueous sodium bicarbonate solution and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with dichloromethane/methanol 95/5 to give the title compound: Rf=0.81 (silica gel, dichloromethane/methanol 95/5).

Workup

temperatureWarm to ambient temperature
filtrationfilter
additiondilute the filtrate with ethyl acetate
extractionExtract the diluted filtrate with a saturated aqueous sodium bicarbonate solution
dry with materialDry the organic layer over Na2SO4
filtrationfilter
customevaporate in vacuo
customto give a residue

Sources & evidence

ORD record: ord-28767a038a794a32816f96fd47d06306
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211199B1

Reaction notes

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