Diisobutylaluminum hydride → Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

HRID 2356054ノート

反応式

HRID 2356054 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:18](OC)=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:19][CH2:18][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 18637399Methyl n-(tert-butoxycarbonyl)-s-phenylcysteinate

生成物 1

HCID 13969831Tert-butyl 2-hydroxy-1-((phenylthio)methyl)ethylcarbamate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of Example 175A (1.22 g, 3.91 mmol) in toluene (10 mL) at −78° C. was treated with 1M DIBAL-H in toluene (8.6 mL), warmed to room temperature over 4 hours, diluted with ethyl acetate (100 mL), washed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product. MS (DCI) m/e 284 (M+H)+.

後処理

  1. washwashed sequentially with 0.1N HCl (30 mL), water (15 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-2cb0fdec93634e24a7a76c6d82e22a9e
出典データセット
uspto-grants-2010_07
特許番号
US07754886B2

反応ノート

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