Water → (2beta,3alpha)-3-Hydroxy-2-(piperazin-1-yl)androstan-17-one

HRID 244249Notes

Reaction equation

HRID 244249 reaction equation
[O:1]1[C@H:3]2[CH2:4][CH:5]3[C@:18]([CH3:20])([CH2:19][C@@H:2]12)[C@@H:17]1[C@H:8]([C@H:9]2[C@@:13]([CH2:15][CH2:16]1)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]2)[CH2:7][CH2:6]3.O.[NH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>ClCCl>[OH:1][C@@H:3]1[C@@H:2]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:19][C@@:18]2([CH3:20])[CH:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:21])[CH2:4]1

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 86660494(2alpha,3alpha)-2,3-Epoxyandrostan-17-one

Product 1

HCID 86660495(2beta,3alpha)-3-Hydroxy-2-(piperazin-1-yl)androstan-17-oneYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

To compound 22 (202 mg, 0.70 mmol) was added water (1 mL) and piperazine (3.5 g, 41 mmol). The solution was subsequently heated at 150° C. over a period of 24 h. The resulting mixture was diluted with dichloromethane (50 mL) and washed with water, dried with Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA) to yield compound 23 (169 mg, 65%). 1H NMR (CDCl3) δ: 0.87 (s, 18-CH3 and 19-CH3), 0.73-2.17 (residual CH and CH2), 2.45, 2.64 and 2.91 (3m, 4×CH2N and 2α-CH), 3.85 (m, 3β-CH).

Workup

  1. washwashed with water
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA)

Sources & evidence

ORD record
ord-9c870cd54c6c47a58d6513727bb6eaac
Source dataset
uspto-grants-2014_02
Patent number
US08653054B2

Reaction notes

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