HCID 86746907, compound → HCID 86746905, compound

HRID 1587148Notes

Reaction equation

HRID 1587148 reaction equation
[OH-].[CH3:2][CH:3]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17]([CH2:18][C@@H:19]([O:29][C:30]([O:32][CH2:33][CH2:34][O:35][P:36]([OH:45])([O:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:43])[CH3:42])=[O:37])=[O:31])[CH2:20][CH2:21]2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])[CH3:4]>CO.[Pd]>[OH-:29].[CH3:4][CH:3]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C@H:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C@H:17]([CH2:18][C@@H:19]([O:29][C:30]([O:32][CH2:33][CH2:34][O:35][P:36]([OH:45])([O:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:42])[CH3:43])=[O:37])=[O:31])[CH2:20][CH2:21]2)[CH2:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])[CH3:2]

Participants

4

Reactant 1

HCID 86746907HCID 86746907, compound

Product 1

HCID 86746905HCID 86746905, compoundYield 119.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1 g of O-[[2-[(cholest-5-en-3β-yloxy)carbonyloxy]ethoxy]hydroxyphosphinyl]choline hydroxide internal salt is hydrogenated in 100 ml of methanol with 1 g of Pd/C 5% under 30 bar of H2 at 80° C. After filtration the solution is evaporated and the residue is dissolved in chloroform-methanol-dioxan. By adding ether there is obtained 0.6 g of O-[[2-[(5α-cholestan-3β-yloxy)carbonyloxy]ethoxy]hydroxyphosphinyl]choline hydroxide internal salt as a hygroscopic powder, m.p. 225° C.

Workup

  1. filtrationAfter filtration the solution
  2. customis evaporated
  3. dissolutionthe residue is dissolved in chloroform-methanol-dioxan
  4. additionBy adding ether there

Sources & evidence

ORD record
ord-bce02de990b54191aa7e03c51437e7fd
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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