Ethyl bromoacetate → 17beta-Ethoxycarbonylmethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

HRID 267619Notes

Reaction equation

HRID 267619 reaction equation
C(N(CC)CC)C.[OH:8][C@@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[C:22](=[O:28])[CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:29]([OH:31])=[O:30])[CH2:10]1.Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CC(C)=O>[CH2:37]([O:36][C:34]([CH2:33][O:30][C:29]([C@H:18]1[CH2:17][CH2:16][C@H:15]2[C@H:14]3[C@H:23]([C:22](=[O:28])[CH2:21][C@:19]12[CH3:20])[C@:24]1([CH3:27])[C@H:11]([CH2:10][C@H:9]([OH:8])[CH2:26][CH2:25]1)[CH2:12][CH2:13]3)=[O:31])=[O:35])[CH3:38]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 227882653alpha-Hydroxy-5alpha-androstan-11-one 17beta-carboxylic acid

Product 1

HCID 13171009117beta-Ethoxycarbonylmethoxycarbonyl-3alpha-hydroxy-5alpha-androstan-11-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Triethylamine (4.5 mmole) was added to a solution of 3α-hydroxy-5α-androstan-11-one 17β-carboxylic acid (1.025g.,) in warm acetone (50 ml.) followed by ethyl bromoacetate (6 mmole) and the reaction mixture stood at room temperature overnight. The reaction was completed by refluxing for 1 hr., evaporating to dryness and partitioning the residue between water and ether. The ethereal solution was washed with water, dried, and evaporated to give a residue (1.61g.) which was purified by preparative t.l.c. to afford the pure title compound; [α]D + 76°.

Workup

  1. temperatureby refluxing for 1 hr
  2. custom, evaporating to dryness
  3. custompartitioning the residue between water and ether
  4. washThe ethereal solution was washed with water
  5. customdried
  6. customevaporated
  7. customto give a residue (1.61g.) which
  8. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-aecb1a5e92cf48438bdade4410df5e6e
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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