2-Methoxypropene → (4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 525516ノート

反応式

HRID 525516 の反応式
[F:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@H:4]([OH:12])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.CO[C:23]([CH3:25])=[CH2:24]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl>[F:1][CH2:2][C@@H:3]1[C@@H:4]([C:5]2[CH:6]=[CH:7][C:8]([I:11])=[CH:9][CH:10]=2)[O:12][C:23]([CH3:25])([CH3:24])[N:13]1[C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20]

参加物

5

反応物 2

HCID 83002-MethoxypropeneHCID 71050029Tert-butyl ((1R,2S)-3-fluoro-1-hydroxy-1-(4-iodophenyl)propan-2-YL)carbamate

生成物 1

HCID 73424774(4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate収率 98.5%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 6344Dichloromethane溶媒

実験手順

A 1 L round bottom flask containing tert-butyl ((1R,2S)-3-fluoro-1-hydroxy-1-(4-iodophenyl)propan-2-yl)carbamate (24.4 g, 61.8 mmol) is charged with CH2Cl2 (250 mL) followed by 2-methoxypropene (9.0 mL, 92.8 mmol). The solution is cooled via ice bath and para toluene sulfonic acid (59 mg, 0.31 mmol) added. The reaction is stirred for 2 hours at room temperature then quenched with saturated sodiumbicarbonate solution (200 mL). The organics were separated, dried over MgSO4 and concentrated to give the title compound (26.5 g): 1H NMR (400 MHz, CDCl3) 7.73 (d, 2H), 7.20 (d, 2H), 5.08 (d, 1H), 5.03-4.69 (m, 1H), 4.54-4.31 (m, 1H), 3.91-3.68 (m, 1H), 1.70 (s, 3H), 1.58 (s, 3H), 1.50 (s, 9H).

後処理

  1. temperatureThe solution is cooled via ice bath
  2. customthen quenched with saturated sodiumbicarbonate solution (200 mL)
  3. customThe organics were separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-e3e6e4b29bf34d87a2764ac4661188ba
出典データセット
uspto-grants-2016_05
特許番号
US09340564B2

反応ノート

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