Benzaldehyde → 2-(Benzylamino)-2-methylpropane-1,3-diol

HRID 584227

Reaction equation

HRID 584227 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]([CH3:15])([CH2:13][OH:14])[CH2:11][OH:12].[BH4-].[Na+].[OH-].[Na+]>CO.C(OCC)(=O)C>[CH2:1]([NH:9][C:10]([CH3:15])([CH2:13][OH:14])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 15312-Amino-2-methyl-1,3-propanediolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 1987392-(Benzylamino)-2-methylpropane-1,3-diol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzaldehyde (17.4 ml) was added dropwise to a solution of 2-amino-2-methyl-1,3-propanediol (20 g) in methanol (200 ml) at 0° C. and the whole was stirred at room temperature for 2 hours. Sodium borohydride (11.5 g) was added thereto in portions at 0° C. and the mixture was stirred for 10 minutes. 1N Sodium hydroxide solution and ethyl acetate were added and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo to give 2-benzylamino-2-methyl-1,3-propanediol (28.54 g).

Workup

  1. stirringin portions at 0° C. and the mixture was stirred for 10 minutes
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-d6eaeaec6c984751a5cd14c9cb938246
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Linked notes

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