11alpha-Hydroxyprogesterone → HCID 18595303, compound

HRID 1580570Notes

Reaction equation

HRID 1580570 reaction equation
[CH3:1][C:2]([C@@H:4]1[C@@:8]2([CH3:24])[CH2:9][C@@H:10](O)[C@@H:11]3[C@:21]4([CH3:22])[C:15](=[CH:16][C:17]([CH2:19][CH2:20]4)=[O:18])[CH2:14][CH2:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].[Cl-].[Li+].[Cl:27]C(F)C(N(CC)CC)(F)F>O1CCCC1>[Cl:27][C@H:10]1[CH2:9][C@@:8]2([CH3:24])[C@@H:7]([CH2:6][CH2:5][C@@H:4]2[C:2](=[O:3])[CH3:1])[C@H:12]2[C@H:11]1[C@:21]1([CH3:22])[C:15]([CH2:14][CH2:13]2)=[CH:16][C:17](=[O:18])[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 9273011alpha-HydroxyprogesteroneHCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amineHCID 433294Lithium Chloride

Product 1

HCID 18595303HCID 18595303, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 11α-hydroxy progesterone (6 g., 0.018 mole), anhydrous lithium chloride (6 g., 0.14 mole), N-(2-Chloro-1,1,2-trifluoroethyl)diethylamine (6 ml., 0.036 mole) and dry tetrahydrofuran (120 ml.) was stirred at -20° for 5 hr. and then room temperature for 16 hr. The reaction mixture was partitioned between methylene chloride and water. Evaporation of the organic layer and chromatography of the residue on magnesium silicate afforded, after recrystallisation from acetone/petroleum ether (b.p. 60°-80°), 11β-chloropregn-4 -ene-3,20-dione (0.26 g., 4%), m.p. 185°-188° [α]D + 252° (c 1.0 CHCl3), λmax. (EtOH) 238 nm. (ε 17,150).

Workup

  1. waitand then room temperature for 16 hr
  2. customThe reaction mixture was partitioned between methylene chloride and water
  3. customEvaporation of the organic layer and chromatography of the residue on magnesium silicate
  4. customafforded
  5. customafter recrystallisation from acetone/petroleum ether (b.p. 60°-80°), 11β-chloropregn-4 -ene-3,20-dione (0.26 g., 4%), m.p. 185°-188° [α]D + 252° (c 1.0 CHCl3), λmax

Sources & evidence

ORD record
ord-3ac3e645b391437e8f6783faf9576343
Source dataset
uspto-grants-1976_01
Patent number
US03933799

Reaction notes

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