4-Nitroperoxybenzoic acid → HCID 86743414, compound

HRID 2350848Notes

Reaction equation

HRID 2350848 reaction equation
[CH:1]([C@@H:4]1[C@H:9]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C@@H:6]([OH:31])[CH2:5]1)[C@:18]1([CH3:19])[C@H:13]([CH2:14][C@H:15]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:16][C@@H:17]1[CH3:23])[CH2:12][CH2:11]3)=[CH:2][CH3:3].[N+](C1C=CC(C(OO)=O)=CC=1)([O-])=[O:33]>C(Cl)CCl>[OH:31][C@H:6]1[CH2:5][C@H:4]([CH:1]2[O:33][CH:2]2[CH3:3])[C@H:9]2[C@H:10]3[C@H:20]([CH2:21][CH2:22][C@:7]12[CH3:8])[C@:18]1([CH3:19])[C@H:13]([CH2:14][C@H:15]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:16][C@@H:17]1[CH3:23])[CH2:12][CH2:11]3

Participants

4

Reactant 2

HCID 703424-Nitroperoxybenzoic acidHCID 70386165HCID 70386165, compound

Product 1

HCID 86743414HCID 86743414, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

36.0 g of 15α-propenyl-17β-hydroxy-1α-methyl-3α-tetrahydropyranyloxy-5α-androstane (German Laid-Open Application 35 39 244, Example 15a) is dissolved in 900 ml of ethylene chloride, combined with 63.0 g of p-nitroperbenzoic acid, and stirred for one hour at 0°-5° C. After dilution with methylene chloride, the mixture is washed with 1-molar sodium hydroxide solution and with water, and evaporated under vacuum. By chromatography on silica gel and crystallization from ether-pentane, 27.7 g of 17β-hydroxy-15α-(1,2-epoxypropyl)-1α-methyl-3α-tetrahydropyranyloxy-5α-androstane is produced, mp 172°-174° C.

Workup

  1. washAfter dilution with methylene chloride, the mixture is washed with 1-molar sodium hydroxide solution and with water
  2. customevaporated under vacuum
  3. customBy chromatography on silica gel and crystallization from ether-pentane

Sources & evidence

ORD record
ord-319c48ad553e4717940359e24e7926d3
Source dataset
uspto-grants-1989_10
Patent number
US04871725

Reaction notes

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