Triphenylphosphine → 3alpha-Azido-5alpha-pregnan-20-one

HRID 1829636

反応式

HRID 1829636 の反応式
O[C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2C(=O)C)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C([O:52][CH2:53][CH3:54])=O)=NC(OCC)=O.C1(P([N:69]=[N+:70]=[N-:71])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:69]([C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:53](=[O:52])[CH3:54])[CH2:3]1)=[N+:70]=[N-:71]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 92787IsopregnanoloneHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3β-hydroxy-5α-pregnan-20-one (60 mg, 0.19 mmol) in THF (2 mL) was treated with triphenylphosphine (100 mg, 0.38 mmol) and diethyl azo-dicarboxylate (0.03 mL, 0.19 mmol). To the resulting solution was added dropwise diphenylphosphoryl azide (0.04 mL, 0.19 mmol) and the mixture was stirred at RT for 24 h. Evaporation of the solvent in vacuo and purification of the residue using flash column chromatography using petroleum ether/ethyl acetate 90/10 as elution solvent afforded the compound named above.

後処理

  1. customEvaporation of the solvent
  2. customin vacuo and purification of the residue
  3. washas elution solvent
  4. customafforded the compound

出典と根拠

ORDレコード
ord-50ff6a499e1248a5b68789a496cc640e
出典データセット
uspto-grants-2006_06
特許番号
US07064116B2

関連ノート

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