Hydrochloric Acid → (17R)-17-Hydroxy-13-propyl-18,19-dinorpregn-4-en-20-yn-3-one

HRID 1077201Notes

Reaction equation

HRID 1077201 reaction equation
[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C:13]4[CH2:14][CH:15]=[C:16]([O:21]C)[CH2:17][C:18]=4[CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@:5]2([C:24]#[CH:25])[OH:23])[CH2:2][CH3:3].Cl.O.CO>CCOCC>[CH2:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@:5]2([C:24]#[CH:25])[OH:23])=[CH:17][C:16](=[O:21])[CH2:15][CH2:14]4)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962Water2×HCID 86733485HCID 86733485, compound

Product 1

HCID 73602799(17R)-17-Hydroxy-13-propyl-18,19-dinorpregn-4-en-20-yn-3-oneYield 33.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Shake 13β-n-propyl-3-methoxy-17β-ethynyl-gona-2,5(10)-dien-17 -ol (0.31 g.) with a solution prepared by mixing concentrated hydrochloric acid (0.81 cc.), water (0.54 cc.) and methanol (12.15 cc.), until the solid dissolves. After addition of water, work up with ether, purify by recrystallization from cyclohexane to obtain the title compound (0.1 g.), m.p. 149°-50.5°; ultraviolet absorption peak at 240 mμ (ε15,700); infrared absorption peaks at 2.99, 3.06, 6.04, 6.16 μ.

Workup

  1. dissolutionuntil the solid dissolves
  2. custompurify by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-38544423709142e38776a2862590a572
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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