Common starting materials

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b-Ketoester:

	Rathke beta-ketoester synthesis.
	Blaise Reaction to make beta-ketoester.

a-Haloketone:



Synth. Commun. 1990, 20 (22), 3489
Synthesis 1982, 12, 1018

Amidine, Oxime amide, Guanidine:

	1.The way of activating amine. Lewis acid could be used to activate nitrile group.
	2. Garigipati Amidine Synthesis.
	3. Pinner amidine synthesis
	4. The concentration of this reaction is critical, using methanol as less as possible.

Procedure 4. Hydroxylamine HCl (1 equiv.) was dissolved into MeOH. To the solution, t-BuOK (1 equiv.) was added. The resulting mixture was stirred at room temperature for 24hours. Nitrile (0.9 equiv.) was added into the mixture, and the resulting mixture was stirred for another 18 hours. After filtering, the filtrate was concentrated. The crude residue was pure enough for next reaction.

Hydrazine:

Amino Acid:

J. Org. Chem. 2000, 65, 8704-8708

1. Strecker amino acid synthesis.

Procedure: To the methanol solution of a ketone (1 equiv.) was added a suspension of NaCN (1.1 equiv.) and NH4Cl. The mixture was stirred for 15 min at room temperature. And then the mixture was heated to 60oC for 24 hours. The reaction was cooled to room temperature, and quenched with water. Ethyl acetate was used to extract the product from aqueous solution. The organic layer was dried, concentrated. To the resulting residue was added concentrated HCl. The resulting mixture was heated to reflux for several hours to afford the amino acid. To the alcohol solution of resulting residue was bubbled HCl gas for 30 min. The resulting mixture was heated to 40oC for another 4 hours to yield ester of amino acid.