HCID 54178539, compound → HCID 11333358, compound

HRID 2256045Notes

Reaction equation

HRID 2256045 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@H:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([OH:23])[CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:23][C@@H:13]1[C@@H:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:16][NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 54178539HCID 54178539, compound

Product 1

HCID 11333358HCID 11333358, compoundYield 117.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3R*,4R*)-1-benzyloxycarbonyl-3-hydroxy-4-phenylpiperidine (0.3 g) in methanol (30 mL) was treated with 10% palladium on carbon (0.03 g) and hydrogenated at atmospheric pressure for 2 hours. The reaction mixture was filtered through diatomaceous earth and evaporated to afford (3R*,4R*)-3-hydroxy-4-phenylpiperidine (0.2 g); MS: m/z=178(M+1); NMR: 1.44-1.58 (m, 2), 2.23-2.5 (m, 9), 4.36 (broad, 1), 7.13-7.29 (m, 5).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customevaporated

Sources & evidence

ORD record
ord-36cd6bbfb6a843ddb13eaa3daf49fe5f
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

Loading…