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

HRID 1829636

반응식

HRID 1829636 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-50ff6a499e1248a5b68789a496cc640e
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064116B2

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