Sodium borohydride → Androstenol

HRID 326980

反応式

HRID 326980 の反応式
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 6852393Androstenone

生成物 1

HCID 101989Androstenol

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

This synthesis is depicted in FIG. 1. Ketone 1 (500 mg, 1.84 mmol) was reduced with sodium borohydride (d, 75 mg, 2 mmol) in THF/MeOH 5:1 (18 ml) at RT. (2 h). The crude product was chromatographed on silica gel (60 g) using toluene/ethyl acetate 2:1. After traces of the axial alcohol 2 (9 mg, 2%), the pure equatorial alcohol 3 (388 mg, 77%) was eluted. An analytical sample was recrystallized from MeOH/water. M.p. 124°-125°, [a]D =+14.2° (c=1.12) ([2]: m.p, 125°-127°, [a]D17 =+11.2° (c=0.76)). - IR. (CDCl3): 3620m, 3430w, 1590w. - 1H-NMR. (360 Mhz): 0.77 (s, 3 H); 0.85 (s, 3 H); 3.60 t x t, J=11 and 5, 1 H); 5.70 (m, 1 H); 5.84 (m,1 H).

後処理

  1. custom(2 h)
  2. customThe crude product was chromatographed on silica gel (60 g)
  3. washAfter traces of the axial alcohol 2 (9 mg, 2%), the pure equatorial alcohol 3 (388 mg, 77%) was eluted
  4. customAn analytical sample was recrystallized from MeOH/water
  5. customM.p. 124°-125°, [a]D =+14.2° (c=1.12) ([2]: m.p, 125°-127°, [a]D17 =+11.2° (c=0.76))

出典と根拠

ORDレコード
ord-67391ce144c749eb8fb18b4a18e726aa
出典データセット
uspto-grants-1993_12
特許番号
US05272134

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