Triethylamine → 17beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267617ノート

反応式

HRID 267617 の反応式
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.C(N(CC)CC)C.[CH2:32](I)[CH2:33][CH2:34][CH3:35]>CC(C)=O>[CH2:32]([O:23][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:24])[CH2:33][CH2:34][CH3:35]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10962Butyl iodideHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

生成物 1

HCID 2278825217beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (521 mg.) in dry acetone (50 ml.) was refluxed with triethylamine (1.04 ml.) and n-butyl iodide (0.87 ml.) for 16 hours. The mixture was evaporated to a residue which was dissolved in chloroform, washed with water, dried (Na2SO4) and evaporated to a foam (534 mg.). A solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water, dried (Na2SO4) and evaporated to give title compound (443 mg.) as a white foam, [α]D + 51°.

後処理

  1. customThe mixture was evaporated to a residue which
  2. dissolutionwas dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a foam (534 mg.)
  6. washA solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated

出典と根拠

ORDレコード
ord-415089cbab4f467e921a99664cf6ae26
出典データセット
uspto-grants-1976_03
特許番号
US03943124

反応ノート

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