Dimethylformamide → HCID 58055032, compound

HRID 2383502Notes

Reaction equation

HRID 2383502 reaction equation
[OH:1][C@@:2]1([CH2:22][CH:23]=[CH2:24])[C@@H:6]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.[H-].[Na+].[CH3:27]N(C=O)C>>[Si:8]([O:7][C@H:6]1[CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3][C@:2]1([O:1][CH3:27])[CH2:22][CH:23]=[CH2:24])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:9])[CH3:10]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 58055034HCID 58055034, compound

Product 1

HCID 58055032HCID 58055032, compound

Procedure

To a solution of tert-butyl (3R,4S)-3-hydroxy-4-(tert-butyldimethylsilyl)oxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate (550 mg) in DMF (10 mL) was added iodemethane (2.2 g) at 0° C. After 10 min, 60% NaH in oil (62 mg) was added, and the mixture was stirred for 1 hour at room temperature. The reaction was quenched with saturated aqueous NH4Cl and the mixture was extracted with Et2O. The extract was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50) to give tert-butyl (3R,4S)-4-(tert-butyldimethylsilyl)oxy-3-methoxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate as a pale yellow foam.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionthe mixture was extracted with Et2O
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with silica gel column chromatography (eluent: hexane/EtOAc=1/0˜50/50)

Sources & evidence

ORD record
ord-27a67a6d37be468fb1f0cb984334129c
Source dataset
uspto-grants-2012_09
Patent number
US08263632B2

Reaction notes

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