Water → HCID 86698314, compound

HRID 1050280Notes

Reaction equation

HRID 1050280 reaction equation
Br[C@@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:4]2([CH3:5])[CH2:3]1)[C:16]1[CH:15]=[CH:14][C:13]([O:20][CH3:21])=[CH:12][C:11]=1[CH2:10][CH2:9]3.[N-:22]=[N+:23]=[N-:24].[Li+].O>CS(C)=O>[N:22]([C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:4]2([CH3:5])[CH2:3]1)[C:16]1[CH:15]=[CH:14][C:13]([O:20][CH3:21])=[CH:12][C:11]=1[CH2:10][CH2:9]3)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 962WaterHCID 88163Lithium azideHCID 67508166HCID 67508166, compound

Product 1

HCID 86698314HCID 86698314, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 1.56 g (4.5 mmol) 16α-bromo-3-methoxy-estra-1,3,5(10)-triene and 0.67 g (13.7 mmol) lithium azide in 30 ml of DMSO is heated for 1 h to 80° C. After cooling, water is added dropwise and the resulting precipitate is collected by filtration, washed with water and dried under vacuum. 1.33 g (96%). F=80-85° C., after recrystallization from ether/methanol: F=84-87° C. [α]D+60° (c=10.2).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customF=80-85° C., after recrystallization from ether/methanol
  6. customF=84-87° C. [α]D+60° (c=10.2)

Sources & evidence

ORD record
ord-2a2a9d93fe004e60a2e0637b6a2778b5
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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