Sodium borohydride → 3-O-Benzyl Estradiol

HRID 1003178노트

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HRID 1003178 반응식
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 11132151(8R,9S,13S,14S)-13-methyl-3-phenylmethoxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one

생성물 1

HCID 112914133-O-Benzyl Estradiol수율 100.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-benzyloxyestra-1,3,5(10)-trien-17-one (40, 2.70 g, 7.5 mmol) in THF (5.0 mL) and MeOH (30 mL) was added sodium borohydride (284 mg, 7.5 mmol) at 0° C. The reaction mixture was stirred for 30 min, then quenched with saturated aqueous NH4Cl, and H2O added. The precipitate was collected by filtration and washed with H2O to afford 2.73 g of 41 (100% yield) mp: 118-119° C.

후처리

  1. customquenched with saturated aqueous NH4Cl, and H2O
  2. additionadded
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O

출처 및 근거

ORD 기록
ord-69a0be22a0734d9ebc507790a65dad55
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06046186

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