Methanol → Melengestrol

HRID 1285319Notes

Reaction equation

HRID 1285319 reaction equation
[CH3:1][C:2]1[C:21]2[C@:16]([CH3:23])([CH2:17][CH2:18][C:19](=[O:22])[CH:20]=2)[C@@H:15]2[C@H:4]([C@H:5]3[C@:12]([CH3:24])([CH2:13][CH2:14]2)[C@@H:8]([C:9](=[O:11])[CH3:10])[CH:7]([CH2:25]SC2C=CC=CC=2)[CH2:6]3)[CH:3]=1.C1(C)C=CC=CC=1.CO.C[O:43]P(OC)OC>C(N(CC)CC)C>[OH:43][C@:8]1([C@:12]2([CH3:24])[C@H:5]([C@H:4]3[C@H:15]([CH2:14][CH2:13]2)[C@:16]2([CH3:23])[C:21](=[CH:20][C:19](=[O:22])[CH2:18][CH2:17]2)[C:2]([CH3:1])=[CH:3]3)[CH2:6][C:7]1=[CH2:25])[C:9](=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 8472Trimethyl phosphiteHCID 18601426HCID 18601426, compound

Product 1

HCID 9906614Melengestrol

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6-Methyl-16-(phenylsulfenylmethyl)-pregna-4,6-diene-3,20-dione (VIA, Example 22, 150 mg), toluene (1.25 ml), methanol (0.216 ml), triethylamine (0.011 ml) and finally trimethylphosphite (0.076 ml) were added to a vial which was sealed, stirred and heated at 100° for 4.75 hr. The mixture was concentrated under reduced pressure to an oil which is TLC'd on silica gel eluting with acetone/methylene chloride (5/95) to give the title compound.

Workup

  1. customwas sealed
  2. temperatureheated at 100° for 4.75 hr
  3. concentrationThe mixture was concentrated under reduced pressure to an oil which

Sources & evidence

ORD record
ord-16cc2908bc544806ad50e3d3e55b55cc
Source dataset
uspto-grants-1986_01
Patent number
US04567001

Reaction notes

Loading…