HCID 58055030, compound → HCID 58055034, compound

HRID 2383501Notes

Reaction equation

HRID 2383501 reaction equation
[Si:1]([O:8][C@@H:9]1[C:13](=[O:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:22]([Mg]Br)[CH:23]=[CH2:24]>C1COCC1>[OH:14][C@@:13]1([CH2:24][CH:23]=[CH2:22])[C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]1

Participants

4

Reactant 2

HCID 58055030HCID 58055030, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 58055034HCID 58055034, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice-cooled solution of tert-butyl (3S)-3-(tert-butyldimethylsilyl)oxy-4-oxopyrrolidine-1-carboxylate (1.2 g) in THF (5 mL) was added dropwise a 1M solution of allylmagnesium bromide in THF (3.8 mL), and the mixture was stirred for 30 min at 0° C. The reaction was quenched with saturated aqueous NH4Cl (5 mL) 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)-3-hydroxy-4-(tert-butyldimethylsilyl)oxy-3-(prop-2-en-1-yl)pyrrolidine-1-carboxylate as a pale yellow foam.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl (5 mL)
  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-c2bde501661b49f88a4a1e2903bea75d
Source dataset
uspto-grants-2012_09
Patent number
US08263632B2

Reaction notes

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