Dichloromethane → HCID 54072020, compound

HRID 343525Notes

Reaction equation

HRID 343525 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.ClCCl.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)([CH2:13][CH2:14][O:15][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chloride2×HCID 81531DiisopropylethylamineHCID 54385751HCID 54385751, compound

Product 1

HCID 54072020HCID 54072020, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent3×

Procedure

Combine (S)-1-(t-butoxycarbonyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (17 g, 47.0 mmol), N,N-diisopropylethylamine (20 mL), and dichloromethane (300 mL). Cool the reaction mixture in an ice bath. Add dropwise methanesulfonyl chloride (4.8 mL). After 30 minutes add additional methanesulfonyl chloride (0.9 mL). After 2 hours, extract the reaction mixture with saturated aqueous sodium bicarbonate solution and then three times with water. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 20% ethyl acetate/hexane, 35% ethyl acetate/hexane, 50% ethyl acetate/hexane and then ethyl acetate to the title compound: Rf =0.24 (silica gel, 35% ethyl acetate/hexane).

Workup

  1. temperatureCool the reaction mixture in an ice bath
  2. extractionextract the reaction mixture with saturated aqueous sodium bicarbonate solution
  3. dry with materialDry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-932bace8f3074c489a9ca74773b0a02c
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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