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

HRID 539989ノート

反応式

HRID 539989 の反応式
[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]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 8058HexaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86691375HCID 86691375、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1918ae492345491fb0c7a39a5188b3ef
出典データセット
uspto-grants-2014_10
特許番号
US08871756B2

反応ノート

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