Benzyl Alcohol → HCID 20434118, compound

HRID 1154606Notes

Reaction equation

HRID 1154606 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]([NH:14][CH2:15][CH:16]([OH:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C(O)C1C=CC=CC=1.[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].C([O-])(=O)C([O-])=O>>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[CH3:3][CH:4]([NH:14][CH2:15][CH:16]([OH:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1

Participants

6

Reactant 5

HCID 244Benzyl AlcoholHCID 971Oxalic AcidHCID 71081OxalateHCID 4311764Sodium borohydrideHCID 13365123HCID 13365123, compound

Product 1

HCID 20434118HCID 20434118, compound

Procedure

20 ml of ethanol are added to the α-(α-methyl-4-methoxyphenethylimino)-2-benzyloxyacetophenone solution obtained in paragraph (2). After ice-cooling, 0.63 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-4-methoxyphenethylamino)methyl]-2-benzyloxybenzylalcohol [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 ethanol. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 2.23 g of α-[(α-methyl-4-methoxyphenethylamino)methyl]-2-benzyloxybenzylalcohol oxalate [the diastereoisomer of M.p. 138°-139° 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 ethanol
  6. customThe crystalline precipitates
  7. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-15d7234c637f46ed8908dd20bef0c736
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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