Triphenylphosphine → 3beta-Acetoxy-14beta-hydroxy-5beta-pregnane-21-nitrile

HRID 1080636Notes

Reaction equation

HRID 1080636 reaction equation
[C:1]([O:4][C@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[CH2:15][CH2:16][N+:17]([O-])=O)[CH2:6]1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[CH2:15][C:16]#[N:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10740169HCID 10740169, compound

Product 1

HCID 107855783beta-Acetoxy-14beta-hydroxy-5beta-pregnane-21-nitrileYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 13.34 g of 3β-acetoxy-21-nitro-5β-pregnane-14β-ol and 39.1 g of triphenylphosphine in 370 ml of dry methylene chloride was kept at 0° C. under nitrogen; 19.3 ml of diethyl azodicarboxylate were added dropwise during 1 hr. After 2 hrs. the solvent was removed in vacuo and the crude product was purified by flash-chromatography (SiO2) using methylene chloride/diethyl ether 95/5 as the eluant to give 11.20 g of 3β-acetoxy-14β-hydroxy-5β-pregnane-21-nitrile.

Workup

  1. customwas kept at 0° C. under nitrogen
  2. customthe solvent was removed in vacuo
  3. customthe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-f883d4eb7b8f4623a587757222550f83
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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