3alpha-Azido-5alpha-pregnan-20-one → 3alpha-Azido-21-bromo-5alpha-pregnan-20-one

HRID 1829637ノート

反応式

HRID 1829637 の反応式
[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH3:15])[CH2:5]1)=[N+:2]=[N-:3].C1C=C[NH+]=CC=1.[Br:32][Br-]Br>C(O)C.C(Cl)(Cl)Cl.ClCCl>[N:1]([C@@H:4]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C@@H:6]([CH2:7][CH2:8][C@@H:9]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C:14](=[O:16])[CH2:15][Br:32])[CH2:5]1)=[N+:2]=[N-:3]

参加物

5

反応物 1

HCID 99460603alpha-Azido-5alpha-pregnan-20-one

生成物 1

HCID 866001863alpha-Azido-21-bromo-5alpha-pregnan-20-one

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3α-azido-5α-pregnan-20-one (51.5 mg, 0.15 mmol) in absolute ethanol (3 mL) and chloroform (3 mL) was added pyridinium bromide perbromide (143 mg, 0.44 mmol) and the resulting mixture was heated at 50° C. for 45 min. Subsequently the mixture was diluted with dichloromethane and the organic layer was washed with water, brine and dried (Na2SO4). Evaporation of the solvent in vacuo and purification of the residue using flash column chromatography and petroleum ether/ethyl acetate 90/10 as elution solvent afforded the compound named above.

後処理

  1. washthe organic layer was washed with water, brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent
  4. customin vacuo and purification of the residue
  5. washas elution solvent
  6. customafforded the compound

出典と根拠

ORDレコード
ord-fd6b8733b58441ce9dbc3401d2248a21
出典データセット
uspto-grants-2006_06
特許番号
US07064116B2

反応ノート

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