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

HRID 52253Notes

Reaction equation

HRID 52253 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 δ0.88 (m, 1.05 (m, 1.30 (m, 1.45 (m, 2H), 1.57 (s, 3H), 1.50-1.75 (m, 5H), 2.10-2.60 (m, 2H), 3.50-4.50 (m, 4H); 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-88964988daa34958923286d38bccbd71
Source dataset
uspto-grants-1997_04
Patent number
US05616612

Reaction notes

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