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Water → (2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine

HRID 975654
Notes
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Reaction equation

HRID 975654 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([N:14]1[CH2:18][C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][C@H:15]1[CH:27]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.C(OCC)(=O)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.CCCCCC>[CH2:7]([N:14]1[CH2:18][C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:16][C@H:15]1[CH:27]=[CH2:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 50922891(2S,4R)-1-benzyl-2-formyl-4-(t-butyldimethylsilyloxy)pyrrolidine

Product 1

HCID 11726876(2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidineYield 83.7%

Reagents, catalysts & solvents 3

HCID 74505
Methyltriphenyliphosphonium bromide
Catalyst
HCID 1140TolueneSolvent
HCID 8058HexaneSolvent

Procedure

To a suspension of methyltriphenylphosphonium bromide (1.07 g) was portionwise added potassium t-butoxide (337 mg) with stirring under ice-cooling. The mixture was stirred at ambient temperature for 2 hours. To the solution cooled on ice-bath was added dropwise (2S,4R)-1-benzyl-2-formyl-4-(t-butyldimethylsilyloxy)pyrrolidine (0.92 g) in toluene (2 ml) and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into a mixture of water (10 ml) and ethyl acetate (20 ml). The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. To the residue was added n-hexane (30 ml). The resulting precipitates were filtered off and the filtrate was evaporated in vacuo. The resulting residue was chromatographed on silica gel (1 g) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyl-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine (765 mg).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at ambient temperature for 2 hours
  3. temperatureTo the solution cooled on ice-bath
  4. stirringthe mixture was stirred at the same temperature for 1 hour
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a residue
  10. customThe resulting precipitates
  11. filtrationwere filtered off
  12. customthe filtrate was evaporated in vacuo
  13. customThe resulting residue was chromatographed on silica gel (1 g)
  14. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
  15. additionThe fractions containing the desired compound
  16. customwere collected
  17. customevaporated in vacuo

Sources & evidence

ORD record
ord-273dfd43d3a74f128e203cba9feace52
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05608056

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes