HCID 70358074, compound → HCID 70358068, compound

HRID 1762569Notes

Reaction equation

HRID 1762569 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:10][CH2:11][C:12]=1[OH:13])=[O:6])[CH3:3]>C(O)C.[Pt]=O>[ClH:1].[CH2:2]([O:4][C:5]([C@H:7]1[C@@H:12]([OH:13])[CH2:11][CH2:10][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

4

Reactant 1

HCID 70358074HCID 70358074, compound

Product 1

HCID 70358068HCID 70358068, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

11.7 g (33 mmol) of 4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-1,2,5,6-tetrahydro-pyridine-3carboxylic acid ethyl ester hydrochloride are hydrogenated at 4.105Pa and room temperature with the addition of 1.2 g of platinum oxide in 300 ml of ethanol. The catalyst is filtered off and the reaction solution is concentrated. Crystallisation from ethanol/diethyl ether yields cis-4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-piperidine-3carboxylic acid ethyl ester hydrochloride of m.p. 156°-160°.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe reaction solution is concentrated
  3. customCrystallisation from ethanol/diethyl ether

Sources & evidence

ORD record
ord-d55de66589b04be693112f0499548eb1
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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