Phenylethanolamine → (R)-(-)-2-Amino-1-phenylethanol

HRID 1860320Notes

Reaction equation

HRID 1860320 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CC1C=CC(O)=CC=1>C(O)CCC>[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 1000PhenylethanolamineHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 6951165(R)-(-)-2-Amino-1-phenylethanolYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

n-Butanol (20 ml) was added with the concentrate of the reaction products obtained in the same manner as in Example 296 which contained 1.67 g (7.50 mmol) of 2-amino-1-phenylethanol, and 2.11 g (7.50 mmol) of Boc-L-Tyr. The resultant mixture was heated for dissolution, cooled to room temperature and left over night to precipitate crystals. The crystals were isolated by filtration to afford 1.06 g (2.10 mmol) of (R)-2-amino-1-phenylethanol.Boc-L-Tyr salt. The yield of the compound based on (R)-2-amino-1-phenylethanol in the concentrate was 56.0%.

Workup

  1. concentrationconcentrate of the reaction products
  2. customobtained in the same manner as in Example 296 which
  3. waitleft over night
  4. customto precipitate crystals
  5. customThe crystals were isolated by filtration

Sources & evidence

ORD record
ord-eca69ceec9c748b48a5c69665c7f4050
Source dataset
uspto-grants-2003_03
Patent number
US06528686B1

Reaction notes

Loading…