Triethylamine → 17beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267617Notes

Reaction equation

HRID 267617 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:21])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:22]([OH:24])=[O:23])[CH2:3]1.C(N(CC)CC)C.[CH2:32](I)[CH2:33][CH2:34][CH3:35]>CC(C)=O>[CH2:32]([O:23][C:22]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([C:15](=[O:21])[CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)=[O:24])[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10962Butyl iodideHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 2278825217beta-n-Butoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3α-hydroxy-11-oxo-5α-androstane-17β-carboxylic acid (521 mg.) in dry acetone (50 ml.) was refluxed with triethylamine (1.04 ml.) and n-butyl iodide (0.87 ml.) for 16 hours. The mixture was evaporated to a residue which was dissolved in chloroform, washed with water, dried (Na2SO4) and evaporated to a foam (534 mg.). A solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water, dried (Na2SO4) and evaporated to give title compound (443 mg.) as a white foam, [α]D + 51°.

Workup

  1. customThe mixture was evaporated to a residue which
  2. dissolutionwas dissolved in chloroform
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to a foam (534 mg.)
  6. washA solution of the foam in ether was washed with saturated sodium bicarbonate solution and with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-415089cbab4f467e921a99664cf6ae26
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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