Methylamine → 17 beta-(Methylamino)estra-1(10),2,4-triene-3,16α-diol

HRID 1065704Notes

Reaction equation

HRID 1065704 reaction equation
C(O)(=O)C.C(O)(=O)C.[OH:9][C:10]1[CH:27]=[CH:26][C:25]2[C@@H:24]3[C@H:15]([C@H:16]4[C@@:20]([CH2:22][CH2:23]3)([CH3:21])[C:19](=O)[C@H:18]([OH:29])[CH2:17]4)[CH2:14][CH2:13][C:12]=2[CH:11]=1.[CH3:30][NH2:31].[BH4-].[Na+]>>[CH3:30][NH:31][C@H:19]1[C@H:18]([OH:29])[CH2:17][C@H:16]2[C@H:15]3[C@H:24]([CH2:23][CH2:22][C@:20]12[CH3:21])[C:25]1[CH:26]=[CH:27][C:10]([OH:9])=[CH:11][C:12]=1[CH2:13][CH2:14]3

Participants

4

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86738380HCID 86738380, compound

Product 1

HCID 986666317 beta-(Methylamino)estra-1(10),2,4-triene-3,16α-diol

Procedure

3,16α-Dihydroxy-oestra-1,3,5(10)-trien-17-one diacetate (32.4 g) was stirred with methylamine solution (324 ml; 33% in EtCH) for 20 min. Sodium borohydride (16.2 g) was added portionwise to the stirred solution, keeping the temperature at <25° C. After 11/2 h., the methylamine was removed under reduced pressure and the residue was acidified with hydrochloric acid (5 N). The mixture was rebasified with saturated potassium bicarbonate solution to give crude product, which was filtered off, washed with water and suspended in methanol. The suspension was boiled for 5 min., cooled and filtered to give pure 17β-methylamino-oestra-1,3,5(10)-triene-3,16α-diol as an amorphous solid (23.5 g; 89%), m.p. 242°-246° C. (decomp.), [α]D +48° (c 1.0 in D.M.S.O.).

Workup

  1. customat <25° C
  2. customAfter 11/2 h., the methylamine was removed under reduced pressure
  3. customto give crude product, which
  4. filtrationwas filtered off
  5. washwashed with water
  6. temperaturecooled
  7. filtrationfiltered

Sources & evidence

ORD record
ord-e0f7f5be2b4d47d9a612a7daf797cae2
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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