Sodium amide → HCID 86751637, compound

HRID 2294697Notes

Reaction equation

HRID 2294697 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH:13]=O)[O:11][C:10]([CH3:16])([CH3:15])[N:9]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].[CH2:25]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:26][CH3:27].[NH2-].[Na+]>O1CCCC1>[CH:13](/[C@H:12]1[O:11][C:10]([CH3:16])([CH3:15])[N:9]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[C@H:8]1[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:25]/[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 80374Propyltriphenylphosphonium bromideHCID 14552357HCID 14552357, compound

Product 1

HCID 86751637HCID 86751637, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.4 g (4.3 mmol) of tert-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (WO 87/05302) and 1.79 g (4.3 mmol) of instantylide, consisting of propyltriphenylphosphonium bromide and sodium amide, in 50 ml of tetrahydrofuran is stirred at room temperature under nitrogen for 30 minutes. Subsequently, the reaction mixture is partitioned between water and ethyl acetate. The organic phase is separated, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on 80 g of silica gel using a 1:1 mixture of methylene chloride and petroleum ether as the eluent. There are obtained 900 mg of tert-butyl (4S,5R)-5-[(Z)-1-butenyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate as a resin; MS: 352 (M+H)+.

Workup

  1. customSubsequently, the reaction mixture is partitioned between water and ethyl acetate
  2. customThe organic phase is separated
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe residue is chromatographed on 80 g of silica gel using
  7. additiona 1:1 mixture of methylene chloride and petroleum ether as the eluent

Sources & evidence

ORD record
ord-ac5b928cb343496094b0b59ca704e19c
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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