Methanol → (R)-2-Amino-1-(3-chlorophenyl)ethanol

HRID 1860319Notes

Reaction equation

HRID 1860319 reaction equation
CO.[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6]>CC(C)CC(=O)C>[NH2:3][CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=1)[OH:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Product 1

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolYield 35.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To 20 ml of methanol were added 1.70 g of the concentrate obtained in the same manner as in Example 295, containing 1.29 g (7.50 mmol) of 2-amino-1-(3-chlorophenyl)ethanol, and 2.88 g (7.50 mmol) of L-di-p-toluoyltartaric acid (hereinafter abbreviated as L-PTTA), and the resultant mixture was heated for dissolution and added with 20 ml of 4-methyl-2-pentanone. The mixture was cooled to room temperature and left over night to give crystals. The crystals precipitated was isolated by filtration to afford 1.69 g (2.63 mmol) of (R)-2-amino-1-(3-chlorophenyl)ethanol.L-PTTA salt. The yield of the compound relative to (R)-2-amino-1-(3-chlorophenyl)ethanol in the concentrate was 70.1%.

Workup

  1. customobtained in the same manner as in Example 295
  2. temperaturewas heated for dissolution
  3. waitleft over night
  4. customto give crystals
  5. customThe crystals precipitated
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-ff4fa8d069584f8aabe09f3575058641
Source dataset
uspto-grants-2003_03
Patent number
US06528686B1

Reaction notes

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