HCID 20434118, compound → HCID 13365124, compound

HRID 1154607Notes

Reaction equation

HRID 1154607 reaction equation
C(O)(=O)C(O)=O.[CH3:7][CH:8]([NH:18][CH2:19][CH:20]([OH:35])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27]CC1C=CC=CC=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1>[C].[Pd].C(O)C>[CH3:7][CH:8]([NH:18][CH2:19][CH:20]([OH:35])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 20434118HCID 20434118, compound

Product 1

HCID 13365124HCID 13365124, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.5 g of α-[(α-methyl-4-methoxyphenethylamino)methyl]-2-benzyloxybenzylalcohol oxalate [the diastereoisomer of M.p. 138°-139° C. (decomp.)], 0.3 g of 10% palladium-carbon and 30 ml of 90% aqueous ethanol is treated in the same manner as described in Example 1-(4-a). The crude product is recrystallized from ethanol in the presence of 300 mg of oxalic acid, and crystalline precipitates are collected by filtration. 0.76 g of α-[(α-methyl-4-methoxyphenethylamino)methyl]-2-hydroxybenzylalcohol 3/2 oxalate [the diastereoisomer of M.p. 175°-176° C. (decomp.)] is thereby obtained.

Workup

  1. additionis treated in the same manner
  2. customThe crude product is recrystallized from ethanol in the presence of 300 mg of oxalic acid
  3. customcrystalline precipitates
  4. filtrationare collected by filtration

Sources & evidence

ORD record
ord-8eb742357f3742ee807c76e8a7ec65fb
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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