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Tetrahedron Letters

Volumn 36, Issue 17, 1995, Pages 2937-2940

Trimethylorthoformate: A mild and effective dehydrating reagent for solution and solid phase imine formation

(4) Look, Gary C a Murphy, Martin M a Campbell, David A a Gallop, Mark A a

a AFFYMAX RESEARCH INSTITUTE (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0028907801 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(95)00442-F Document Type: Article

Times cited : (154)

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13
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- In general, the free base of the amine component is used. However, we have run experiments using amino acids which were converted to their free bases in situ. When the solubility of the amino acid salt is not an issue, we obtain comparable results to that of the independently generated free base amino acids.

14
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- G. Look and C. Holmes, unpublished results.

15
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- Trimethylorthoformate-mediated in situ reductive amination reactions is the subject of another paper.

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24
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- General Procedure for Imine Formation in Solution Phase. The amino acid alkyl ester (4 mmol) was added to a stirred solution of trimethylorthoformate (8–10 mL). After 5 min, benzaldehyde (4 mmol) was added and the mixture stirred for 8 hours. The mixture was taken up in ethyl ether (25 mL) and extracted with water (4 × 50 mL), dried over anhydrous magnesium sulfate, concentrated and analyzed without further purification.

25
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