Sodium Sulfate → HCID 10889034, compound

HRID 2176460Notes

Reaction equation

HRID 2176460 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:17]([O:19][C:20](=[O:23])[CH:21]=O)[CH3:18]>C1(C)C=CC=CC=1>[CH2:17]([O:19][C:20](=[O:23])[CH:21]=[N:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])[CH3:18]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 70211Ethyl oxoacetateHCID 6431891-Phenethylamine, (+)-

Product 1

HCID 10889034HCID 10889034, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (R)-1-phenyl-ethylamine (59 g, 0.49 mmol) dissolved in toluene (500 mL) was added sodium sulfate (173 g, 1.22 mmol) followed by oxo-acetic acid ethyl ester (134 g, 0.49 mmol, 50% in toluene) dropwise. The reaction mixture was stirred at RT for 1 h. The solid was filtered and the filtrate was concentrated under vacuum to provide ((R)-1-phenyl-ethylimino)-acetic acid ethyl ester, which was dissolved in DMF (300 mL) at RT. TFA (56 g, 0.49 mmol) was added dropwise at RT, followed after 10 min by cyclopenta-1,3-diene (65 g, 0.98 mmol) and water (0.25 ml). The mixture was stirred at RT overnight, concentrated under vacuum and the residue was poured into a 10% aqueous solution of NaHCO3 (500 mL). The solution was adjusted to pH 8 with solid Na2CO3, and extracted with EtOAc (3×80 mL). The combined organic layers were purified by silica gel chromatography (30:1-15:1 petroleum ether:EtOAc) to provide the title intermediate (35 g, 26% yield), as a colorless oil. (m/z): [M+H]+ calcd for C17H21NO2 272.16 found 272.2.

Workup

  1. filtrationThe solid was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-5ef2ec2454704b14a547d50c6d3aea65
Source dataset
uspto-grants-2015_06
Patent number
US09066944B2

Reaction notes

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