(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxaldehyde → (4S)-alpha-Ethyl-2,2-dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

HRID 1781345Notes

Reaction equation

HRID 1781345 reaction equation
[CH3:1][C:2]1([CH3:17])[N:6]([C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C@H:5]([CH:15]=[O:16])[CH2:4][O:3]1.[CH3:18][CH2:19][Mg+].[Br-]>CCOCC>[CH2:18]([CH:15]([C@@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:17])[N:6]1[C:7](=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[OH:16])[CH3:19]

Participants

4

Reactant 2

HCID 53905465(S)-2,2-Dimethyl-3-(1-oxoheptyl)-4-oxazolidinecarboxaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 57042123(4S)-alpha-Ethyl-2,2-dimethyl-3-(1-oxoheptyl)-4-oxazolidinemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 9a (108 mg, 0.44 mmol) in ether (1 mL) is added dropwise to a cold (5°) solution of EtMgBr (3M in ether, 0.36 mL). The cold bath is removed, a crystal of iodine is added to the mixture and stirring is continued for 1.5 h at room temperature. The resulting mixture is diluted with EtOAc and washed with saturated aqueous NH4Cl solution. The aqueous phase is reextracted and the combined organic solution dried and evaporated to yield crude 10a: NMR δ 0.88 (m, 3 H), 1.05 (m, 3 H), 1.30 (m, 6 H), 1.45 (m, 2 H), 1.57 (s, 3 H), 1.50-1.75 (m, 5 H), 2.10-2.60 (m, 2 H), 3.50-4.50 (m, 4 H); MS (EI) m/z 271 (M).

Workup

  1. customThe cold bath is removed
  2. additiona crystal of iodine is added to the mixture
  3. additionThe resulting mixture is diluted with EtOAc
  4. washwashed with saturated aqueous NH4Cl solution
  5. customthe combined organic solution dried
  6. customevaporated

Sources & evidence

ORD record
ord-ba83b90f82aa43f2bdb332b49d366c08
Source dataset
uspto-grants-1997_05
Patent number
US05633280

Reaction notes

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