Hydrazine hydrate (1:1) → HCID 15819148, compound

HRID 1050285Notes

Reaction equation

HRID 1050285 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 21723401HCID 21723401, compound

Product 1

HCID 15819148HCID 15819148, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5.0 g 16α-azido-3-methoxy-estra-1,3,5(10)-triene-17β-ol, 100 ml methanol, 10 ml of 80% hydrazine hydrate and 4 spatula tips of Raney nickel are heated for 30 min on a water bath. Purification and recrystallization are performed as described for the purification of 16α-amino-3-methoxy-estra-1,3,5(10)-triene-17β-ol. Yield: 3.2 g (69%). F=158-161° C.; [α]D+41° (pyridine). IR: 3367 (NH). 3601 (OH);

Workup

  1. customPurification and recrystallization
  2. customas described for the purification of 16α-amino-3-methoxy-estra-1,3,5(10)-triene-17β-ol
  3. customF=158-161° C.

Sources & evidence

ORD record
ord-86510775a7bf4c2f9858c25d90d8dffd
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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