Triethylamine → HCID 60209506, compound

HRID 1267092Notes

Reaction equation

HRID 1267092 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:8]([CH2:18][OH:19])[CH2:7]1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][C@H:6]1[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[C@H:8]([CH2:18][O:19][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 60209505HCID 60209505, compound

Product 1

HCID 60209506HCID 60209506, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-4-(3,4-dichlorobenzyl)-1-tert-butoxycarbonyl-2-(hydroxymethyl)pyrrolidine (1.38 g, 3.82 mmol) in methylene chloride (30 mL) was added triethylamine (0.78 mL, 5.72 mmol) followed by methanesulfonyl chloride (0.36 mL, 4.58 mmol) and the mixture was stirred at 20° for 9 hrs. Most CH2Cl2 was then removed by evaporation in vacuo, and the residue was diluted with ethyl acetate and washed with aqueous NaHCO3 followed by water. Drying with Na2SO4 followed by evaporation in vacuo gave 1.70 g of crude (2S,4R)-4-(3,4-dichlorobenzyl)-1-tert-butoxycarbonyl-2-(methanesulfonyloxymethyl)pyrrolidine, which was used without further purification.

Workup

  1. customMost CH2Cl2 was then removed by evaporation in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with aqueous NaHCO3
  4. dry with materialDrying with Na2SO4
  5. customfollowed by evaporation in vacuo

Sources & evidence

ORD record
ord-76ea2f2b54054f46a02c766e286024bd
Source dataset
uspto-grants-2003_04
Patent number
US06552028B2

Reaction notes

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