Allyl bromide → HCID 69793034, compound

HRID 1743236Notes

Reaction equation

HRID 1743236 reaction equation
[CH2:1]([C@H:8]1[C:12](=[O:13])[O:11][C@@H:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:9]1[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:34](Br)[CH:35]=[CH2:36].[Cl-].[NH4+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:36]([C@:8]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:12](=[O:13])[O:11][C@@H:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:9]1[C:18]([O:20][CH2:21][CH:22]=[CH2:23])=[O:19])[CH:35]=[CH2:34]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 69793074HCID 69793074, compound

Product 1

HCID 69793034HCID 69793034, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.16 g of allyl (2S,4S)-4-benzyl-2-tert-butyl-5-oxooxazolidine-3-carboxylate in 20 ml of tetrahydrofuran are cooled in a dry ice bath to −65° C. under argon, and 20.9 ml of a 0.5 molar solution of potassium bistrimethylsilylamide in toluene are added dropwise, and the mixture is stirred at this temperature for 30 minutes. Then 0.861 ml of allyl bromide are added dropwise, and the mixture is stirred while gradually warming to room temperature. After being left to stand overnight, 15 ml of saturated ammonium chloride solution were added, and the product was extracted with ethyl acetate. Washing of the ethyl acetate solution with saturated brine was followed by evaporation in vacuo and purification of the product by column chromatography (silica gel, mobile phase: ethyl acetate:heptane=5:45).

Workup

  1. stirringthe mixture is stirred
  2. waitAfter being left
  3. waitto stand overnight
  4. extractionthe product was extracted with ethyl acetate
  5. washWashing of the ethyl acetate solution with saturated brine
  6. customwas followed by evaporation in vacuo and purification of the product by column chromatography (silica gel, mobile phase: ethyl acetate:heptane=5:45)

Sources & evidence

ORD record
ord-f55bf70dc11842a5b191902a8dbceb78
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

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