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

HRID 1871196Notes

Reaction equation

HRID 1871196 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH2:21][O:22][S:31]([CH3:30])(=[O:33])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 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

To a solution of N-t-butoxycarbonyl-4(R)-t-butyldimethylsilyloxy-2(S)-hydroxymethylpyrrolidine (50.0 g, 150.8 mmol) and triethylamine (42.0 ml, 300 mmol) in CH2Cl2 (11) was added methane sulfonyl chloride (12.4 ml, 160 mmol) over a period of 5 minutes and stirring was continued for 1 hour. The solvent was evaporated in vacuo diluted with EtOAc (800 mL) and washed sequentially with aqueous citric acid and NaHCO3. The organic extracts were dried (Na2SO4), evaporated in vacuo and the residue purified by chromatography (SiO2, 15% EtOAc in hexanes). The title compound was obtained as a pale yellow solid FAB Mass spectrum, m/z=410(M+1).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additiondiluted with EtOAc (800 mL)
  3. washwashed sequentially with aqueous citric acid and NaHCO3
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. customevaporated in vacuo
  6. customthe residue purified by chromatography (SiO2, 15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e471511fb31b448e868cf8675f4b0695
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

Loading…