p-Toluenesulfonic acid monohydrate → (S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamate

HRID 711999ノート

反応式

HRID 711999 の反応式
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH:14]=[CH2:15])[CH2:4][O:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C([O-])(O)=O.[Na+]>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH:14]=[CH2:15]

参加物

5

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11020618tert-Butyl (4S)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

生成物 1

HCID 11041481(S)-tert-butyl 1-hydroxybut-3-en-2-ylcarbamate収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of tert-butyl (4S)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (1.90 g, 8.36 mmol) in methanol (83 mL) was added p-toluenesulfonic acid monohydrate (0.80 g, 4.2 mmol) at 0° C. The mixture was slowly warmed to room temperature overnight. The reaction mixture was diluted with saturated NaHCO3 solution, concentrated, and then diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3 (2×) and brine, dried over Na2SO4, filtered and concentrated to give the desired product as colorless oil (1.187 g, 76%). 1H NMR (400 MHz, CDCl3) δ 5.81 (1H, m), 5.25 (2H, m), 4.90 (1H, m), 4.25 (1H, br s), 3.67 (2H, m), 1.45 (9H, s) ppm.

後処理

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with sat. NaHCO3 (2×) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ccef6943f9134345a3d6f95c5d259238
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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