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

HRID 726135노트

반응식

HRID 726135 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6c66fbcbf77e44e28af67cf917a3ccce
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05708001

반응 노트

불러오는 중…