Diazomethane → Norprostol

HRID 918274Notes

Reaction equation

HRID 918274 reaction equation
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.[N+](=[CH2:19])=[N-]>CO>[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:19])=[O:15])=[CH:3]1

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 3690897ACMC-20apjz

Product 1

HCID 3912664Norprostol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1.0 part of 3(RS)-hydroxy-5-oxocyclopent-1-eneheptanoic acid dissolved in methanol is added dropwise a 5% ethereal diazomethane solution until a slight excess of diazomethane is present. That excess is detected when the solution exhibits a persistent yellow color. The solution then is evaporated to dryness under a nitrogen atmosphere to yield methyl 3(RS)-hydroxy-5-oxocyclopent-1-eneheptanoate.

Workup

  1. customThe solution then is evaporated to dryness under a nitrogen atmosphere

Sources & evidence

ORD record
ord-c866e62f543c400785b024198c7e5702
Source dataset
uspto-grants-1976_07
Patent number
US03970683

Reaction notes

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