1-Butanol → 5alpha-Hydroxy-6beta-(3-propylamino)-cholestan-3beta-ol

HRID 64386

反応式

HRID 64386 の反応式
[O:1]1[C@H:3]2[CH2:4][C@@H:5]3[C@@H:21]([C@@:22]4([CH3:28])[CH2:23][CH2:24][C@H:25]([OH:27])[CH2:26][C:2]124)[CH2:20][CH2:19][C@@:18]1([CH3:29])[C@H:6]3[CH2:7][CH2:8][C@@H:9]1[C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15].[NH2:30][CH2:31][CH2:32][C:33]1C2C(=CC=CC=2)NC=1.C(O)CCC>COC(C)(C)C>[OH:1][C@:2]12[CH2:26][C@@H:25]([OH:27])[CH2:24][CH2:23][C@:22]1([CH3:28])[C@@H:21]1[C@H:5]([C@H:6]3[C@:18]([CH3:29])([CH2:19][CH2:20]1)[C@@H:9]([C@H:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:8][CH2:7]3)[CH2:4][C@H:3]2[NH:30][CH2:31][CH2:32][CH3:33]

参加物

5

反応物 3

HCID 2631-ButanolHCID 1150TryptamineHCID 1888556a-Cholesterol oxide

生成物 1

HCID 1176425225alpha-Hydroxy-6beta-(3-propylamino)-cholestan-3beta-ol収率 71.5%

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

5,6α-epoxicholestan-3β-ol (8.9 g, 22.1 mmol, 1 eq) and tryptamine (7.1 g, 44.1 mmol, 2 eq) were charged in a round-bottomed flask equipped with a magnetic stirrer bar. 1-Butanol (70 ml, 5 vol) was added and the mixture heated to reflux for 40 h. The reaction mixture was cooled at r.t., diluted with methyl-tertbutyl-ether (5 vol) and washed with water (5 vol) and with brine (5 vol). The organic layer was passed through a silica pad (40 g) eluted with methyl-tertbutyl-ether (3 vol) then 10% Methanol/ethyl acetate (60 vol). Fractions of interest were pooled and the solvent was removed under reduced pressure to give 5α-Hydroxy-6β-(3-propylamino)-cholestan-3β-ol as a white solid (7.3 g, 59%). In same conditions, use of ethanol as solvent (40 vol) and Ca(OTf)2 as catalyst gave a 21% yield.

後処理

  1. customequipped with a magnetic stirrer bar
  2. temperaturethe mixture heated
  3. temperatureto reflux for 40 h
  4. washwashed with water (5 vol) and with brine (5 vol)
  5. washeluted with methyl-tertbutyl-ether (3 vol)
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-1cff756c6f4b46999d9fa25a03a809ec
出典データセット
uspto-grants-2016_09
特許番号
US09447141B2

関連ノート

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