Chlorotrimethylsilane → (R)-3-((2S,3S,E)-2-allyl-3-hydroxy-5-phenylpent-4-enoyl)-4-benzyloxazolidin-2-one

HRID 56401

Reaction equation

HRID 56401 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:19])[CH2:15][CH2:16][CH:17]=[CH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Mg+2].[Cl-].[Na].C(N(CC)CC)C.[CH:31](=[O:40])/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl[Si](C)(C)C>C(OCC)(=O)C>[CH2:16]([C@@H:15]([C@@H:31]([OH:40])/[CH:32]=[CH:33]/[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:14]([N:9]1[C@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:19])[CH:17]=[CH2:18]

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 637511CinnamaldehydeHCID 5360315Magnesium ChlorideHCID 5360545SodiumHCID 10858190(R)-4-Benzyl-3-pent-4-enoyloxazolidin-2-one

Product 1

HCID 67113561(R)-3-((2S,3S,E)-2-allyl-3-hydroxy-5-phenylpent-4-enoyl)-4-benzyloxazolidin-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of (R)-4-benzyl-3-pent-4-enoyloxazolidin-2-one (50 g, 193 mmol), magnesium chloride (18.3 g, 193 mmol), sodium hexafluorostibate(V) (14.9 g, 58 mmol), triethylamine (80 mL, 579 mmol), (trans)-cinnamaldehyde (30.6 g, 232 mmol) and chlorotrimethylsilane (37.2 mL, 290 mmol) in ethyl acetate (500 mL) was stirred at room temperature for 17 hours. The mixture was diluted with ethyl acetate and filtered to remove solids. The filtrate was concentrated to small volume, and then diluted with methanol (500 mL) and a small amount of ethyl acetate. After treatment with trifluoroacetic acid (3 mL), the resulting solution was stirred at room temperature for 1 h, and then concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10) to afford the title compound (60 g, 80%) as a yellow semi-solid. MS (ES+) C24H25NO4 requires: 391, found: 374 [M+H−H2O]+.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. concentrationThe filtrate was concentrated to small volume
  4. additiondiluted with methanol (500 mL)
  5. stirringAfter treatment with trifluoroacetic acid (3 mL), the resulting solution was stirred at room temperature for 1 h
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10)

Sources & evidence

ORD record
ord-4c695542b1dc42d2a9c99d233bd7e03b
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Linked notes

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