Methanol → HCID 21714030, compound

HRID 650241Notes

Reaction equation

HRID 650241 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)CC=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21](OC)([O:24][CH3:25])[O:22][CH3:23].[CH3:28]O>CCCCCC.C(OCC)(=O)C.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH2:1]([O:8][C:9]([NH:11][CH:15]([C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:28]=1)[CH:21]([O:24][CH3:25])[O:22][CH3:23])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 9005Trimethyl orthoformateHCID 21560562HCID 21560562, compound

Product 1

HCID 21714030HCID 21714030, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-Benzyloxycarbonylphenylglycinal (1.38 g, 5.12 mmol) was dissolved in methanol (2.6 ml), and trimethyl orthoformate (1.12 ml, 10.24 mmol) and camphor sulfonic acid (59.5 mg, 0.256 mmol) were added to it and stirred overnight at room temperature. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by column chromatography on alumina (50 g alumina, hexane/ethyl acetate=2/1) whereby the title compound (1.21 g, 77% yield) was obtained.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-589ad9bfb9ef42aa9fc472863eb17792
Source dataset
uspto-grants-2001_08
Patent number
US06271238B1

Reaction notes

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