Acetic Anhydride → HCID 22826492, compound

HRID 543648Notes

Reaction equation

HRID 543648 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[N:8]1([C@H:14]2[CH2:31][C@@:30]3([CH3:32])[C@@H:17]([CH2:18][CH2:19][C@@H:20]4[C@@H:29]3[CH2:28][CH2:27][C@@:25]3([CH3:26])[C@H:21]4[CH2:22][C@H:23]([N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[C@@H:24]3[OH:33])[CH2:16][CH2:15]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1>[C:1]([O:33][C@H:24]1[C@@H:23]([N:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[CH2:22][C@H:21]2[C@H:20]3[C@H:29]([CH2:28][CH2:27][C@:25]12[CH3:26])[C@:30]1([CH3:32])[C@H:17]([CH2:16][CH2:15][C@@H:14]([N:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)[CH2:31]1)[CH2:18][CH2:19]3)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 22826493HCID 22826493, compound

Product 1

HCID 22826492HCID 22826492, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (1.21 ml) was added to a solution of 2β,16β-di-(1-piperidinyl)-5α-androstan-17β-ol (3.77 g) in dry pyridine (75 ml) at 0°-5° C. and the solution was set aside at room temperature for 19 h. Saturated sodium carbonate solution (40 ml) was added to precipitate the product, which was filtered off and washed well with water (200 ml). A solution of the crude product in diethyl ether (50 ml) was washed with water (2×100 ml), dried (MgSO4) and concentrated to afford 2β,16β-di-(1-piperidinyl)-5α-androstan-17β-ol acetate (3.91 g), m.p. 156°-161° C.; [α]D +28.7° (c 0.47 in CHCl3).

Workup

  1. customto precipitate the product, which
  2. filtrationwas filtered off
  3. washwashed well with water (200 ml)
  4. washA solution of the crude product in diethyl ether (50 ml) was washed with water (2×100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-71aaea57b4cc48f8aff96e1647c5b2b7
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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