4-Benzylphenol → (S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 749930ノート

反応式

HRID 749930 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=2)=[CH:5][CH:6]=1.[H-].[Na+].[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH2:29]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[C:17]([O:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[CH2:29][O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[CH:13][CH:12]=1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

参加物

5

反応物 3

HCID 75634-BenzylphenolHCID 24758Sodium hydrideHCID 11783214tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

生成物 1

HCID 44819340(S)-2-(4-Benzyl-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester収率 117.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of 4-hydroxydiphenylmethane (0.77 g, 4.18 mmol) in anhydrous DMF (22.5 mL) at 0° C. was added a 60% dispersion of NaH in mineral oil (0.23 g, 5.75 mmol) portionwise over 5 min. The resulting slurry was stirred at 0° C. for 45 minutes before a solution of tosylate from step 1 (1.50 g, 4.22 mmol) in DMF (11 mL) was added dropwise over 5 min. The subsequent mixture was stirred at 60° C. overnight. The reaction mixture was poured over ice and then concentrated under reduced pressure. The crude residue was extracted into ethyl acetate and sequentially washed with water, saturated aq. NaHCO3, water and brine. The combined organic layer was dried anhydrous Na2SO4, filtered and concentrated in vacuo to afford the title compound (1.8 g, >100%) as a tan oil;

後処理

  1. additionwas added dropwise over 5 min
  2. additionThe reaction mixture was poured over ice
  3. concentrationconcentrated under reduced pressure
  4. extractionThe crude residue was extracted into ethyl acetate
  5. washsequentially washed with water, saturated aq. NaHCO3, water and brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-015ec1289363454b997671bb4c8d9def
出典データセット
uspto-grants-2008_07
特許番号
US07402684B2

反応ノート

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