17beta-Carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one → 17Hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene

HRID 726135ノート

反応式

HRID 726135 の反応式
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3)(OC)=[O:2].[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl>[OH:2][CH2:1][CH:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][CH:16]([OH:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3

参加物

4

反応物 2

HCID 1000287217beta-Carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-oneHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 2288120817Hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 17β-carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (2.30 g, 5.33 mmol), example 1, part E, in methylene chloride (70 mL) at -78° C. is treated with diisobutylaluminum hydride (1.5M in toluene, 15 mL, 22.5 mmol). After 20 minutes the reaction is quenched with methanol (4 mL), methylene chloride added (150 mL), washed with 2N NaOH and water, dried over MgSO4 and concentrated to give crude 17hydroxymethyl-3-hydroxy-6-t-butoxycarbonyl-6-azaandrost-4-ene of sufficient purity to carry on to the following steps; yield: 2.16 g (99%).

後処理

  1. customAfter 20 minutes the reaction is quenched with methanol (4 mL), methylene chloride
  2. additionadded (150 mL)
  3. washwashed with 2N NaOH and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6c66fbcbf77e44e28af67cf917a3ccce
出典データセット
uspto-grants-1998_01
特許番号
US05708001

反応ノート

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