Hydrazine hydrate (1:1) → HCID 15819149, compound

HRID 1050286Notes

Reaction equation

HRID 1050286 reaction equation
[N:1]([C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+]=[N-].O.NN>[Ni].CO>[NH2:1][C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[C@H:5]1[OH:24])[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21723406HCID 21723406, compound

Product 1

HCID 15819149HCID 15819149, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.0 g 16β-azido-3-methoxy-estra-1,3,5(10)-triene-17β-ol are reduced with 20 ml methanol, 2 ml 80% hydrazine hydrate and one spatula tip of Raney nickel by procedures as described for the purification of 16β-Amino-3-methoxy-estra-1,3,5(10)-triene-17α-ol. Recrystallization is performed from methanol/ether. Yield: 0.7 g (76%). F=152-157° C.; [α]D+59° (pyridine). IR: 3300 (broad), 3417 (OH, NH), 3601 (OH).

Workup

  1. customas described for the purification of 16β-Amino-3-methoxy-estra-1,3,5(10)-triene-17α-ol
  2. customRecrystallization
  3. customF=152-157° C.

Sources & evidence

ORD record
ord-5367dd7baf2b468ab88457f2c36830a7
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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