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

HRID 1779885Notes

Reaction equation

HRID 1779885 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-66688beb34724859873f119b6cfa5d9a
Source dataset
uspto-grants-1997_05
Patent number
US05629200

Reaction notes

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