Benzyl 3-phenylpropanoate → (S)-4-(N-methylindol-3-ylmethyl)-2-(2-phenylethyl)-1,3-oxaz oline

HRID 1365106Notes

Reaction equation

HRID 1365106 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](OCC2C=CC=CC=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][C@H:30]([NH2:33])[CH2:31][OH:32])=[CH:21]1>ClC1C=CC=CC=1>[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][C@H:30]2[CH2:31][O:32][C:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:33]2)=[CH:21]1

Participants

4

Reactant 2

HCID 562789Benzyl 3-phenylpropanoateHCID 67111552(S)-2-(N-methylindol-3-ylmethyl)-2-aminoethanol

Product 1

HCID 57815586(S)-4-(N-methylindol-3-ylmethyl)-2-(2-phenylethyl)-1,3-oxaz olineYield 76%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of benzyl 3-phenylpropionate (1.5 mmol), (S)-2-(N-methylindol-3-ylmethyl)-2-aminoethanol (1.5 mmol), Zn4(OCOCF3)6O (0.15 mmol) and chlorobenzene (2.5 mL) was heated under reflux for 18 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel column chromatography to give (S)-4-(N-methylindol-3-ylmethyl)-2-(2-phenylethyl)-1,3-oxazoline in 76% yield. The compound was identified by comparison with physical property data of the known compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customFrom the resulting solution, the solvent was removed
  4. customan evaporator
  5. customthe residues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-487ebbc3681646819f11cd2819b29423
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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