3-Methoxy-9alpha-hydroxyandrosta-3,5-dien-17-one → 20-Isocyano-3-methoxypregna-3,5,17(20)-trien-9alpha-ol

HRID 1613984Notes

Reaction equation

HRID 1613984 reaction equation
[OH:1][C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=O)[C@@H:11]1[CH2:10][CH:9]=[C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6]([O:21][CH3:22])=[CH:7]1.[N+:24]([CH:26](P(=O)(OCC)OCC)[CH3:27])#[C-:25]>>[N+:24]([C:26](=[C:15]1[C@:16]2([CH3:17])[C@H:12]([C@H:11]3[C@:2]([OH:1])([CH2:19][CH2:18]2)[C@:3]2([CH3:23])[C:8]([CH:7]=[C:6]([O:21][CH3:22])[CH2:5][CH2:4]2)=[CH:9][CH2:10]3)[CH2:13][CH2:14]1)[CH3:27])#[C-:25]

Participants

3

Reactant 2

HCID 108600603-Methoxy-9alpha-hydroxyandrosta-3,5-dien-17-oneHCID 11745449Diethyl alpha-isocyanoethylphosphonate

Product 1

HCID 5704764620-Isocyano-3-methoxypregna-3,5,17(20)-trien-9alpha-olYield 69%

Procedure

Using the procedure of Example 27, 3.10 g of 9α-hydroxy-3-methoxyandrosta-3,5-dien-17-one and 8.02 g of diethyl α-isocyanoethylphosphonate were reacted for 5 hours to produce 2.39 g of the title compound as a mixture of 2 diastereomers. Chromatography was performed on silica gel with toluene/acetone 9/1 containing 0,1% triethylamine as eluent.

Workup

  1. customwere reacted for 5 hours

Sources & evidence

ORD record
ord-7ebd3773f8cc48ab8fd52588e37cace4
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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