HCID 67220664, compound → HCID 67219934, compound

HRID 1838733Notes

Reaction equation

HRID 1838733 reaction equation
[BrH:1].C([N:9]1[CH2:14][C@@H:13]([CH2:15][OH:16])[C@H:12]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C@@H:11]([OH:24])[CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[BrH:1].[OH:16][CH2:15][C@@H:13]1[CH2:14][NH:9][CH2:10][C@H:11]([OH:24])[C@H:12]1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 67220664HCID 67220664, compound

Product 1

HCID 67219934HCID 67219934, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The solution of 18.6 g (47.2 mmol) of crude (3R,4R,5S)-1-benzyl-5-hydroxymethyl-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrobromide in 250 ml of methanol was flushed with argon, treated with 1.5 g of palladium-on-charcoal (10%) and exhaustively hydrogenated at room temperature under normal pressure during 18 hours. The reaction mixture was filtered over Dicalit and the residue washed twice with 100 ml of warm methanol. The methanol solutions were combined and evaporated under reduced pressure to yield 12.79 g of (3R,4R,5S)-5-hydroxymethyl-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrobromide [MS: 223 (M)+] as a yellowish foam which was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered over Dicalit
  2. washthe residue washed twice with 100 ml of warm methanol
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6fadd788cd7247768599ea16045df4d2
Source dataset
uspto-grants-2004_01
Patent number
US06673931B2

Reaction notes

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