Water → HCID 22868545, compound

HRID 232759

Reaction equation

HRID 232759 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.O.[O:12]1[C@H:14]2[CH2:15][C@H:16]3[C@:29]([CH3:31])([CH2:30][C@@H:13]12)[C@@H:28]1[C@H:19]([C@H:20]2[C@@:24]([CH2:26][CH2:27]1)([CH3:25])[C@@H:23]([OH:32])[C@@H:22]([N:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:21]2)[CH2:18][CH2:17]3>C(#N)C>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C@H:13]3[CH2:30][C@@:29]4([CH3:31])[C@@H:16]([CH2:17][CH2:18][C@@H:19]5[C@@H:28]4[CH2:27][CH2:26][C@@:24]4([CH3:25])[C@H:20]5[CH2:21][C@H:22]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)[C@@H:23]4[OH:32])[CH2:15][C@@H:14]3[OH:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 160638722Alpha,3alpha-epoxy-16beta-(1-pyrrolidinyl)-5alpha-androstan-17beta-OL

Product 1

HCID 22868545HCID 22868545, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After adding 63 g of 1,4-dioxa-8-azaspiro[4.5]decane and 13 ml of water to 17 g of 2α,3α-epoxy-16β-(1-pyrrolidinyl)-5α-androstane-17β-ol, the reaction mixture is maintained at 100° to 105° C. for 80 hours while introducing nitrogen. After completion of the reaction, the solution containing a precipitate is diluted with 200 ml of acetonitrile and after filtering, the precipitate is thoroughly washed with water and then with acetonitrile, dried and recrystallized from methanol to give the title product in a yield of 18.2 g (76.5%), m.p.: 184°-187° C.

Workup

  1. temperaturethe reaction mixture is maintained at 100° to 105° C. for 80 hours
  2. additionwhile introducing nitrogen
  3. customAfter completion of the reaction
  4. additionthe solution containing a precipitate
  5. filtrationafter filtering
  6. washthe precipitate is thoroughly washed with water
  7. dry with materialwith acetonitrile, dried
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-d432d9d21a9f4e12b3cc1722ac9e8480
Source dataset
uspto-grants-1997_01
Patent number
US05591735

Linked notes

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