Water → HCID 54424644, compound

HRID 1003193Notes

Reaction equation

HRID 1003193 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[N+:28]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].O>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[NH2:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 69335442HCID 69335442, compound

Product 1

HCID 54424644HCID 54424644, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3-benzyloxy4-nitroestra-1,3,5(10)-trien-17-one (84, 3.24 g, 8.0 mmol) in acetone (400 mL) were added 0.5 N aqueous NaOH (100 mL, 50 mmol) and sodium hydrosulfite (85%, 10 g) at 80° C.; the mixture was then stirred for 1 h. After the reaction mixture was cooled to room temperature, H2O (300 mL) was added; Acetone was then removed at reduced pressure, and the mixture allowed to stand for 3 h at 0° C. The precipitate was collected by filtration and washed with H2O to afford 2.29 g of 85 (76% yield) mp: 219-221° C.

Workup

  1. customAcetone was then removed at reduced pressure
  2. waitto stand for 3 h at 0° C
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O

Sources & evidence

ORD record
ord-3012dc9540d148f2807ca763cb7d68be
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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