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

HRID 539989노트

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HRID 539989 반응식
[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]

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8058HexaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86691375HCID 86691375, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1918ae492345491fb0c7a39a5188b3ef
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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