Propionyl chloride → HCID 67897746, compound

HRID 329960Notes

Reaction equation

HRID 329960 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[Br-:6].[OH:7][C@@H:8]1[C@@H:25]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:24][C@@:23]2([CH3:32])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][C@H:16]([N+:38]3([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)[C@@H:17]2[O:33][C:34](=[O:37])[CH2:35][CH3:36])[CH2:9]1>ClCCl>[Br-:6].[N:26]1([C@H:25]2[CH2:24][C@@:23]3([CH3:32])[C@@H:10]([CH2:11][CH2:12][C@@H:13]4[C@@H:22]3[CH2:21][CH2:20][C@@:18]3([CH3:19])[C@H:14]4[CH2:15][C@H:16]([N+:38]4([CH3:44])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]4)[C@@H:17]3[O:33][C:34](=[O:37])[CH2:35][CH3:36])[CH2:9][C@@H:8]2[O:7][C:1](=[O:4])[CH2:2][CH3:3])[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 67897850HCID 67897850, compound

Product 1

HCID 67897746HCID 67897746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Propanoyl chloride (5.24 ml) was added to a solution of 1-[(2β,3α,5α,16β,17β)-3-hydroxy-2(4-morpholinyl)-17-(1-oxopropoxy)-androstan-16-yl]-1-methylpiperidinium bromide (2.62 g) in dichloro-methane (33 ml) and the solution was set aside at room temperature for 20 h. The solution was evaporated to dryness under reduced pressure to give a gum, which was taken up in dichloromethane (15 ml) and purified by chromatography on alumina (Fluka type 5016A) (62 g) to give 1-[(2β,3α,5α,16β,17β)-2-(4-morpholinyl)-3,17-bis(1-oxopropoxy)-androstan-16-yl]-1-methylpiperidinium bromide as a non-crystalline solid (1.99 g), [α]D20 =-16.7° (c 1.09 in CHCl3).

Workup

  1. customThe solution was evaporated to dryness under reduced pressure
  2. customto give a gum, which
  3. custompurified by chromatography on alumina (Fluka type 5016A) (62 g)

Sources & evidence

ORD record
ord-6275d8d0bbdb4cef9bd8bb1487cb3657
Source dataset
uspto-grants-1990_01
Patent number
US04894369

Reaction notes

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