(3aS,7aS)-2-Allyl-1,3-bis(4-bromobenzyl)-2-chlorooctahydro-1H-benzo[d][1,3,2]diazasilole → (R)-4-((R)-1-hydroxybut-3-enyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 2208974Notes

Reaction equation

HRID 2208974 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([N:11]2[C:15](=[O:16])[CH2:14][C@@H:13]([CH:17]=[O:18])[CH2:12]2)[CH3:10])=[CH:5][CH:4]=1.[CH2:19]=[CH:20][CH2:21][Si]1(Cl)N(CC2C=CC(Br)=CC=2)[C@@H]2[C@H](CCCC2)N1CC1C=CC(Br)=CC=1>>[OH:18][C@@H:17]([C@H:13]1[CH2:12][N:11]([C@@H:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH3:10])[C:15](=[O:16])[CH2:14]1)[CH2:21][CH:20]=[CH2:19]

Participants

3

Reactant 2

HCID 11467036(3aS,7aS)-2-Allyl-1,3-bis(4-bromobenzyl)-2-chlorooctahydro-1H-benzo[d][1,3,2]diazasiloleHCID 117842859(R)-1-((R)-1-(4-Methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde

Product 1

HCID 117843150(R)-4-((R)-1-hydroxybut-3-enyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

Procedure

To a solution of (R)-1-((R)-1-(4-methoxyphenyl)ethyl)-5-oxopyrrolidine-3-carbaldehyde 1.07 (0.93 g, 3.76 mmol) at rt was added (S,S)-2-allyl-1,3-bis-(4-bromobenzyl)-2-chlorooctahydro-2-1H-1,3,2-benzodiazasilole (3.338 g, 6.02 mmol) followed by Sc(III) triflate (0.093 g, 0.188 mmol). The reaction was stirred at rt for 1.5 hr and the solvent was removed. To the residue was added Et2O (80 mL) and 1M HCl (20 mL). The suspension was stirred for 1 hr and the solids were removed by filtration. The filter cake was washed with ether. The filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was further extracted with Et2O (3×40 mL). The combined organics were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography to afford (R)-4-((R)-1-hydroxybut-3-enyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 1.08.

Workup

  1. customthe solvent was removed
  2. additionTo the residue was added Et2O (80 mL) and 1M HCl (20 mL)
  3. stirringThe suspension was stirred for 1 hr
  4. customthe solids were removed by filtration
  5. washThe filter cake was washed with ether
  6. customThe filtrate was transferred to a separatory funnel
  7. customthe layers were separated
  8. extractionThe aqueous layer was further extracted with Et2O (3×40 mL)
  9. dry with materialThe combined organics were dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3f581741ab6640228daed94465b4fcb1
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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