Acetone → HCID 67684264, compound

HRID 232761Notes

Reaction equation

HRID 232761 reaction equation
[CH2:1]([Br:4])[CH:2]=[CH2:3].[O:5]1[C:9]2([CH2:14][CH2:13][N:12]([C@H:15]3[CH2:32][C@@:31]4([CH3:33])[C@@H:18]([CH2:19][CH2:20][C@@H:21]5[C@@H:30]4[CH2:29][CH2:28][C@@:26]4([CH3:27])[C@H:22]5[CH2:23][C@H:24]([N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)[C@@H:25]4[OH:34])[CH2:17][C@@H:16]3[OH:40])[CH2:11][CH2:10]2)[O:8][CH2:7][CH2:6]1.[CH3:41][C:42](CC(O)=O)=[O:43].[CH3:48][C:49](C)=[O:50]>>[Br-:4].[C:42]([O:40][C@@H:16]1[C@@H:15]([N:12]2[CH2:11][CH2:10][C:9]3([O:8][CH2:7][CH2:6][O:5]3)[CH2:14][CH2:13]2)[CH2:32][C@@:31]2([CH3:33])[C@@H:18]([CH2:19][CH2:20][C@@H:21]3[C@@H:30]2[CH2:29][CH2:28][C@@:26]2([CH3:27])[C@H:22]3[CH2:23][C@H:24]([N+:35]3([CH2:1][CH:2]=[CH2:3])[CH2:36][CH2:37][CH2:38][CH2:39]3)[C@@H:25]2[O:34][C:49](=[O:50])[CH3:48])[CH2:17]1)(=[O:43])[CH3:41]

Participants

4

Reactant 3

HCID 180AcetoneHCID 7841Allyl bromideHCID 131719763HCID 131719763, compound

Product 1

HCID 67684264HCID 67684264, compound

Procedure

After adding 20 ml of allyl bromide to a solution containing 13 g of 2β-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-16β-(1-pyrrolidinyl)-5α-androstane-3α,17β-diol-diacetate in 100 ml of acetone, the reaction mixture is kept for 24 hours at room temperature. After completion of the reaction, the product is precipitated by ether, filtered, washed with a mixture of ether and acetone until it becomes free from allyl bromide and dried. The quaternary compound (13.4 g) thus obtained is purified by chromatography on a silica gel column. After evaporating the combined fraction containing the aimed product, the residue is recrystallized from a mixture of acetone and ether to obtain the title product in a yield of 9 g (55.8%), m.p.: 186°-189° C.

Workup

  1. customAfter completion of the reaction
  2. customthe product is precipitated by ether
  3. filtrationfiltered
  4. washwashed with a mixture of ether and acetone until it
  5. customdried

Sources & evidence

ORD record
ord-3349ae71414e4ca48b89b781a6ce291c
Source dataset
uspto-grants-1997_01
Patent number
US05591735

Reaction notes

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