Methanol → 3-O-Benzyl Estradiol

HRID 1660713ノート

反応式

HRID 1660713 の反応式
[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.CO.[BH4-].[Na+]>C1COCC1>[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

参加物

5

反応物 3

HCID 887MethanolHCID 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

生成物 1

HCID 112914133-O-Benzyl Estradiol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of 3-benzyloxyestra-1,3,5(10)-trien-17-one BLE99049 (3.46 g, 9.59 mmol) in THF (15 ml) and MeOH (38 ml) was added sodium borohydride (0.36 g, 9.58 mmol) at 0° C. The reaction mixture was stirred for 30 min at room temperature, then quenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O added. The precipitate was collected by filtration and washed with H2O to afford 3.50 g of 3-benzyloxyestra-1,3,5(10)-trien-17β-ol BLE99051 (100% crude yield) as a white solid.

後処理

  1. customquenched with 10 ml of saturated aqueous NH4Cl and 50 ml of H2O
  2. additionadded
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O

出典と根拠

ORDレコード
ord-818618f2fe9741ea83ffd94b6c26a69c
出典データセット
uspto-grants-2011_10
特許番号
US08030296B2

反応ノート

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