Benzyl Alcohol → HCID 13365121, compound

HRID 1154614Notes

Reaction equation

HRID 1154614 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([NH:16][CH2:17][CH:18]([OH:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1.C(O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(O)(=O)C(O)=O.C([O-])(=O)C([O-])=O>>[CH3:3][CH:4]([NH:16][CH2:17][CH:18]([OH:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

6

Reactant 5

HCID 244Benzyl AlcoholHCID 971Oxalic AcidHCID 71081OxalateHCID 4311764Sodium borohydrideHCID 13365126HCID 13365126, compound

Product 1

HCID 13365121HCID 13365121, compound

Procedure

30 ml of ethanol are added to the α-(α-methyl-3,4-dimethoxyphenethylimino)-2-methoxyacetophenone solution obtained in paragraph (2). After ice-cooling, 1.53 g of sodium borohydride is added gradually to the solution, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is treated in the same manner as described in Example 1-(3), whereby α-[(α-methyl-3,4-dimethoxyphenethylamino)methyl]-2-methoxybenzylalcohol [the mixture of two diastereoisomers] is obtained as a crude oil. Said benzylalcohol [i.e., the mixture of two diastereoisomers] is treated with oxalic acid to convert it into its oxalate, and the oxalate is recrystallized from 70% aqueous ethanol. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 4.5 g of α-[(α-methyl-3,4-dimethoxyphenethylamino)methyl]-2-methoxybenzylalcohol 1/2 oxalate [the diastereoisomer of M.p. 199°-200° C. (decomp.)] are thereby obtained.

Workup

  1. temperatureAfter ice-cooling
  2. additionThe reaction mixture is treated in the same manner
  3. customis obtained as a crude oil
  4. additionthe mixture of two diastereoisomers]
  5. customthe oxalate is recrystallized from 70% aqueous ethanol
  6. customThe crystalline precipitates
  7. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-1e9bb14b116f4264b8106a7e5ee1db4b
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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