Water → HCID 69334834, compound

HRID 1003190Notes

Reaction equation

HRID 1003190 reaction equation
[CH2:1]([O:8][C:9]1[C:26]([N+:27]([O-])=O)=[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:30])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[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[C:26]([NH2:27])=[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:30])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 69334435HCID 69334435, compound

Product 1

HCID 69334834HCID 69334834, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3-benzyloxy-2-nitroestra-1,3,5(10)-trien-17-one (79, 1.82 g, 4.5 mmol) in acetone (250 mL) were added 0.5 N aqueous NaOH (60 mL, 30 mmol) and sodium hydrosulfite (85%, 6.0 g) at 80° C., and stirred for 1 h. After the reaction mixture was cooled to room temperature, H2O (150 mL) was added, acetone was removed at reduced pressure, and the remainder allowed to stand for 3 h at 0° C. The precipitate was collected by filtration and washed with H2O to afford 1.15 g of 80 (68% yield) mp: 205-207° C.

Workup

  1. customacetone was 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-6032dd2cd07b43c291e2a7acfd96d22c
Source dataset
uspto-grants-2000_04
Patent number
US06046186

Reaction notes

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