Triethylamine → Ammonia

HRID 2230574Notes

Reaction equation

HRID 2230574 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:16][CH2:17][OH:18])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].CO.ClCCl>ClCCl>[NH3:11].[C:1]([N:11]1[CH2:15][CH2:14][C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([CH2:16][CH2:17][O:18][S:33]([CH3:32])(=[O:35])=[O:34])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 184649261-Carbobenzyloxy-3-phenyl-3-(2-hydroxyethyl)pyrrolidineHCID 21226129Dichloromethane methanol

Product 2

HCID 222AmmoniaYield 1%HCID 184651041-Carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 1-carbobenzyloxy-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (9.6 g, 29.6 mmol) and triethylamine (8.2 mL, 59.2 mmol) in dichloromethane (150 mL). Cool in an ice-bath. Add methanesulfonyl chloride (2.5 mL, 32.6 mmol). After 16 hours, dilute the reaction mixture with dichloromethane and extract with brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give residue. Chromatograph the residue on silica gel eluting with methanol/dichloromethane 1/10 containing 1% concentrated aqueous ammonia to give 1-carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine.

Workup

  1. temperatureCool in an ice-bath
  2. extractionextract with brine
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give residue

Sources & evidence

ORD record
ord-92304a637b2e480685238c8d2210d921
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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