HCID 11779758, compound → HCID 10335383, compound

HRID 1494118Notes

Reaction equation

HRID 1494118 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH:10]([OH:22])[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH:2]=1>[Pd].C(O)C>[OH:22][CH:10]([CH2:9][CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1

Participants

4

Reactant 1

HCID 11779758HCID 11779758, compound

Product 1

HCID 10335383HCID 10335383, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7.36 g (24 mmol) 1-(3-pyridyl)-4-hydroxy-8-(2-tetrahydropyranyloxy)-1-octyne, 100 mL ethanol and 0.74 g 10% palladium on charcoal is hydrogenated in a Parr apparatus at 3 atmospheres pressure and room temperature for 8 hours. The catalyst is filtered off and washed with ethanol. The combined filtrate is evaporated to give 5-hydroxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane; NMR (CDCl3) delta 4.4 (brs,1H), 2.67 (t,2H).

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed with ethanol
  3. customThe combined filtrate is evaporated

Sources & evidence

ORD record
ord-31e0db549024462fa65b74240311d9e9
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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