Water → HCID 22826493, compound

HRID 543647Notes

Reaction equation

HRID 543647 reaction equation
C(O[C@H:5]1[C@@H:10]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:9][C@H:8]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:6]12[CH3:7])[C@:25]1([CH3:26])[C@H](CCC(=O)[CH2:24]1)CC3)(=O)C.[OH2:31]>N1CCCCC1.C(O)=O>[N:11]1([C@H:10]2[CH2:24][C@@:25]3([CH3:26])[C@@H:6]([CH2:29][CH2:28][C@@H:17]4[C@@H:27]3[CH2:28][CH2:29][C@@:6]3([CH3:7])[C@H:8]4[CH2:9][C@H:10]([N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[C@@H:5]3[OH:31])[CH2:8][CH2:9]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 962WaterHCID 70501193HCID 70501193, compound

Product 1

HCID 22826493HCID 22826493, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8082PiperidineSolvent

Procedure

A solution of 17β-acetyloxy-16β-(1-piperidinyl)-5α-androstan-2-one (8.24 g) in piperidine (36 ml) and formic acid (12 ml) was heated at reflux temperature under a nitrogen (oxygen-free) atmosphere for 4.5 h. When the solution had cooled to room temperature, water (50 ml) was added to precipitate the product, which was filtered off and washed well with water (300 ml). A solution of the crude product in diethyl ether (60 ml) was washed with water (2×100 ml), dried (MgSO4) and evaporated to dryness. Crytsllisation of the residue from acetone afforded 2β,16β-di-(1-piperidinyl)-5α-androstan-17β-ol (4.17 g), m.p. 176°-181° C.; [α]D +41.3° (c 0.59 in CHCl3).

Workup

  1. temperatureat reflux temperature under a nitrogen (oxygen-free) atmosphere for 4.5 h
  2. customto precipitate the product, which
  3. filtrationwas filtered off
  4. washwashed well with water (300 ml)
  5. washA solution of the crude product in diethyl ether (60 ml) was washed with water (2×100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3f1671251f0844c3998b0b89aed72fb9
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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