Hydrochloric Acid → HCID 14076759, compound

HRID 568790Notes

Reaction equation

HRID 568790 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]=O.[NH2:12][C@@H:13]([CH3:16])[CH2:14][OH:15].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:12][C@@H:13]([CH3:16])[CH2:14][OH:15]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 80307L-AlaninolHCID 5003444Sodium cyanoborohydrideHCID 22379768(2,3-Dichlorophenyl)acetaldehyde

Product 1

HCID 14076759HCID 14076759, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 13.0 g (0.074 mole) of crude 2,3-dichlorobenzeneacetaldehyde in 50 ml of MeOH was added 5.7 ml (0.074 mole) of (S)-2-amino-1-propanol. The reaction was placed under an atmosphere of argon and 3.6 g (0.058 mole) of sodium cyanoborohydride was added. After stirring for 2.5 hr, the reaction was made acidic by adding ethereal hydrogen chloride. After stirring of 30 min enough 3N sodium hydroxide was added to make the reaction basic. The reaction mixture was extracted with ether and the ether layer was washed with water, brine and dried (K2CO3). Evaporation of the solvent in vacuo gave a yellow oil. The oil was treated with ethereal hydrogen chloride and the solid was collected. The solid was recrystallized from 2-propanol to give 5.10 g of the title compound (28% yield), mp 148°-151° C.

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ether
  3. washthe ether layer was washed with water, brine
  4. dry with materialdried (K2CO3)
  5. customEvaporation of the solvent in vacuo
  6. customgave a yellow oil
  7. customthe solid was collected
  8. customThe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-cf25344dc02943c2a3cfbd324f11469e
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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