Ammonium Chloride → (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

HRID 725944Notes

Reaction equation

HRID 725944 reaction equation
C(N(CC)C(C)C)(C)C.[S:10](Cl)([CH3:13])(=[O:12])=[O:11].[C:15]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@H:23]1[CH2:35][OH:36])=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl-].[NH4+]>C(Cl)Cl>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH2:24][C@H:23]1[CH2:35][O:36][S:10]([CH3:13])(=[O:12])=[O:11])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 14117008(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N-Diisopropylethylamine (21.1 ml, 121 mmol) and mesyl chloride (4.67 ml, 60.3 mmol) were successively added to a solution of (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-hydroxymethylpyrrolidine (10.2 g, 30.2 mmol; the compound of Reference Example 1-3) in European Laid Open Patent Application No. 449191) in methylene chloride (200 ml) in a nitrogen stream under cooling with ice and the resulting liquid mixture was stirred at the same temperature for 30 minutes. To this reaction solution, saturated aqueous ammonium chloride was added to terminate the reaction. The reaction mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-(mesyloxymethyl)pyrrolidine as the residue.

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2a3eaad780954472a6061a20d43599aa
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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