Dichloromethane → Ammonia

HRID 2230573Notes

Reaction equation

HRID 2230573 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].ClCCl>CC(C)=O.O.CO.ClCCl>[NH3:9].[C:21]([N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 184645642-(3-Phenylpyrrolidin-3-yl)ethanol

Product 2

HCID 222AmmoniaYield 1%HCID 184649261-Carbobenzyloxy-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 18366337Propan-2-one--water (1/1)SolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (prepared by extraction from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (20 g, 32.8 mmol) and sodium bicarbonate (16.5 g, 197 mmol) in acetone/water (160 mL/80 mL). Add dropwise benzyl chloroformate (4.7 mL, 32.8 mmol). After 16 hours, evaporate the reaction mixture in vacuo to give a residue. Combine the residue and dichloromethane, extract with water and then brine, to give a residue. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give residue. Chromatograph the residue on silica gel eluting with methanol/dichloromethane 1/7 containing 1% concentrated aqueous ammonia to give 1-carbobenzyloxy-3-phenyl-3-(2-hydroxyethyl)pyrrolidine.

Workup

  1. customevaporate the reaction mixture in vacuo
  2. customto give a residue
  3. extractionextract with water
  4. custombrine, to give a residue
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo
  8. customto give residue

Sources & evidence

ORD record
ord-69bbc74d92de48719a5ab740f1d1106b
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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