Bromocyclopentane → HCID 68147995, compound

HRID 1606294Notes

Reaction equation

HRID 1606294 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@H:7]([CH2:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:20])[CH:13]=[C:14]([OH:19])[C:15]=43)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].C(OC1C2[C@@H]3[C@@H]([C@H:34]4[C@@:38](CC3)(C)[C@@H:37](OC(=O)C)[CH2:36][CH2:35]4)CCC=2C=C(OC(=O)C)C=1)(=O)C.[CH:52]1(Br)[CH2:56][CH2:55][CH2:54][CH2:53]1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.C(O)C>[CH:52]1([O:19][C:14]2[C:15]3[C@@H:16]4[C@@H:7]([C@H:6]5[C@@:2]([CH2:18][CH2:17]4)([CH3:1])[C@@H:3]([OH:21])[CH2:4][CH2:5]5)[CH2:8][CH2:9][C:10]=3[CH:11]=[C:12]([O:20][CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38]3)[CH:13]=2)[CH2:56][CH2:55][CH2:54][CH2:53]1

Participants

7

Reactant 4

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 68147230HCID 68147230, compoundHCID 70617801HCID 70617801, compound

Product 1

HCID 68147995HCID 68147995, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 850 mg. of 8α-estra-1,3,5(10)-triene-1,3,17β-triol (prepared from compound of Example 10 by saponification in 30 ml. of ethanol is heated to the boiling point under N2 with 2.5 ml. of cyclopentyl bromide and 2.5 g. of potassium carbonate for 5 hours. The mixture is then introduced into ice water, taken up in ether, and the organic phase is washed, dried, and evaporated. After purification by chromatography on silica gel, 365 mg. of final product is obtained.

Workup

  1. washthe organic phase is washed
  2. customdried
  3. customevaporated
  4. customAfter purification by chromatography on silica gel, 365 mg

Sources & evidence

ORD record
ord-10a2e3190e1a42d7940aa30d3cec1803
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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