Tetrahydrofuran → tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 539989Notes

Reaction equation

HRID 539989 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[Na+].CC[CH2:13][CH2:14][CH2:15][CH3:16].C([C@H]1C[O:22][C:21]([CH3:25])([CH3:24])[N:20]1[C:26]([O-:28])=[O:27])=O.O1[CH2:33][CH2:32][CH2:31]C1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:15]([C@H:14]1[CH2:13][O:22][C:21]([CH3:24])([CH3:25])[N:20]1[C:26]([O:28][C:32]([CH3:31])([CH3:33])[CH3:1])=[O:27])=[CH2:16]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86691375HCID 86691375, compound

Product 1

HCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylateYield 83.9%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a solution of methyltriphenylphosphonium bromide (3.1 g, 8.64 mmol) in dry tetrahydrofuran (30 mL) was add a solution of sodium bis(trimethylsilyl)amide in hexane (1.0 M, 8.64 mL, 8.64 mmol) under argon. After the reaction was stirred for further 20 minutes, a solution of (4R)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.8 g, 7.86 mmol) in dry tetrahydrofuran (20 mL) was added dropwise. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified by flash column to give tert-butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.5 g, 83.9%) as colorless liquid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-1918ae492345491fb0c7a39a5188b3ef
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

Loading…