Norethisterone Acetate → 3-Oxo-17beta(1oxopropoxy)androst-4en-19-al

HRID 973095

Reaction equation

HRID 973095 reaction equation
[CH3:1][C@@:2]12[C@:10]([OH:13])(C#C)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:14][CH2:15][C:16]3[C@@H:22]([C@H:5]1[CH2:4][CH2:3]2)[CH2:21][CH2:20][C:18](=[O:19])[CH:17]=3.CC([O:26][C@:27]1(C#C)[C@@]2(C)CC[C@@H]3[C@@H]4C(=CC(CC4)=O)CC[C@H]3[C@@H]2[CH2:29][CH2:28]1)=O.C[C@@]12[C@:57]([OH:60])(C#C)CC[C@H]1[C@@H]1CCC3CC(=O)CCC=3[C@H]1CC2.CC(O[C@@H]1C=C2[C@@H]([C@@H]3[C@@H](CC2)[C@@H]2CC[C@@](OC(C)=O)(C#C)[C@@]2(C)CC3)CC1)=O.CC(=O)[C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)CC2)CC3)CC1.C(O)(=O)C.O[C@]1([C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)CC2)[C@@H](C)C3)CC1)C(=O)C.C(O)(=O)C.O[C@]1([C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(=CC(=O)CC2)C(C)=C3)CC1)C(=O)C.O.O[C@@]1(C#CC)CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)C(=CC(=O)CC1)[C@@H](C)C3.CC[C@@]12[C@](O)(C#C)CC[C@H]1[C@@H]1CCC3[C@@H]([C@H]1CC2)CCC(=O)C=3.CC(=O)[C@@H]1[C@]2(C)[C@H]([C@H]3[C@@H](CC2)[C@@]2(C)C(=CC(=O)CC2)C=C3)CC1>>[O:19]=[C:18]1[CH2:20][CH2:21][C@@:22]2([CH:57]=[O:60])[C:16]([CH2:15][CH2:14][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[O:13][C:27](=[O:26])[CH2:28][CH3:29])=[CH:17]1

Participants

11

Reactant 10

HCID 5832Norethisterone AcetateHCID 5994ProgesteroneHCID 6230NorethindroneHCID 6231NorethynodrelHCID 9051DydrogesteroneHCID 9270Ethynodiol DiacetateHCID 13109LevonorgestrelHCID 65320Dimethisterone MonohydrateHCID 66742607acetic acid;(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-oneHCID 131710941acetic acid;(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one

Product 1

HCID 867345753-Oxo-17beta(1oxopropoxy)androst-4en-19-al

Procedure

The composition of claim 25 wherein the progestogen is 17-hydroxy-19-nor-17α-pregn-4-en-20yn-3-one, 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one acetate, 17-hydroxy-19-nor-17α-pregn-5(10)en-20-yn-3-one, 17-hydroxy-19-nor-17α-pregn-4-en-20-yn, 19-nor-17α-pregn-4-en-20-yne-3β,17-diol diacetate, 3-cyclopentyloxy-19-nor-17α-pregna-3,5-diene-20-yn-17-ol acetate, 16α(R),17-](1phenylethylidene)bis(oxy)]pregn-4-ene-3,20-dione, 17-hydroxy-6α-methylpregn-4-ene-3,20-dione acetate, 17α-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate, 17α-hydroxy-6-methyl-16-methylene-4,6-diene-3,20-dione acetate, 17β-hydroxy-6α-methyl-17-(1-propynyl)androst-4-en-3-one monohydrate, 13-ethyl-17-hydroxy-18,19-dinor-17α-pregn-4-en-20-yn-3-one, or 9β,10α-pregna-4,6-diene-3,20-dione.

Sources & evidence

ORD record
ord-b4931d9b65a3428f98c87b516a03f09a
Source dataset
uspto-grants-1977_10
Patent number
US04054651

Linked notes

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