2-Amino-1-butanol, (-)- → HCID 135767964, compound

HRID 2210314Notes

Reaction equation

HRID 2210314 reaction equation
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[C:7]([C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=O)[C:12]=1[OH:19])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([C:11]1[CH:18]=[CH:17][CH:16]=[C:13]([CH:14]=[N:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])[C:12]=1[OH:19])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 27238562-Amino-1-butanol, (-)-HCID 36786753-tert-Butyl-2-hydroxybenzaldehyde

Product 1

HCID 135767964HCID 135767964, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

0.98 g of (R)-2-amino-1-butanol and 1.78 g of 3-tertbutylsalicylaldehyde were disolved in 15 ml of methanol to prepare a methanol solution. The methanol solution was heated under reflux over 6 hours to obtain a reaction mixture. The solvent of the mixture was removed by distillation in vacuo to obtain a concentrated solution. The concentrated solution was placed on a silica gel column and eluted with a mixture of hexane and ethyl acetate (hexane:ethyl acetate=3:1) to give 2.04 g of (R)-2-[N-(3-tert-butylsalicylidene)amino]-1-butanol as yellow syrup (yield: 82%).

Workup

  1. temperatureunder reflux over 6 hours
  2. customto obtain a reaction mixture
  3. customThe solvent of the mixture was removed by distillation in vacuo
  4. customto obtain a concentrated solution
  5. washeluted with a mixture of hexane and ethyl acetate (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-cddc1f5528df47e8968241e2713fd11e
Source dataset
uspto-grants-1995_10
Patent number
US05457225

Reaction notes

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