1-Phenethylamine, (+)- → (R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester

HRID 497488Notes

Reaction equation

HRID 497488 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][O:9][CH2:8][C:7]1=O)=[O:5])[CH3:2].[CH3:13][C@@H:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][O:9][CH2:8][C:7]=1[NH:21][C@@H:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 21362493Ethyl 3-oxooxane-4-carboxylate

Product 1

HCID 59042158(R)-5-(1-Phenyl-ethylamino)-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl esterYield 104.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 3-oxo-tetrahydro-pyran-4-carboxylic acid ethyl ester (3.03 g, 17.6 mmol), R-(+)-α-methylbenzylamine (2.35 g, 19.4 mmol) and p-toluenesulfonic acid hydrate (67 mg, 230 μmol) in benzene (60 mL) was heated at reflux under a Dean-Stark trap for 16 h. The cooled mixture was concentrated in vacuo to provide the product as a yellow oily semisolid (5.05 g), used without further purification.

Workup

  1. temperatureat reflux under a Dean-Stark trap for 16 h
  2. concentrationThe cooled mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d8ea3ca2c62b46d9898cacf81f00f3a6
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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