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16th September 2016 @ 06:57

Synthesis begun on 9/13

Reaction Scheme:

 

Compound

MW (g/mol)

Mol (mmol)

g

Density (g/mL)

Volume (mL)

eqv

2-chloro-6-hydrazinylpyrazine

(MRLS 1-2)

144.56

3.805 mmol

0.55

 

 

1

Tertbutyl 3-formylpiperidine-1-carboxylate

213.27

4 mmol

0.8531g

 

 

1

3% EtOH in H2O

60.05

 

 

 

0.7

 

Acetonitrile

41.05

 

 

 

10  ml

 

Product

339.82

3.805

1.293 g

 

 

 1

 MRLS 1-2 (0.5493 g, 3.805 mmol) was stirred in 3% EtOH (0.7 mL) and MeCN (10 mL). Tertbutyl 3-formylpiperidine-1-carboxylate (0.8519 g, 4 mmol) was added to the suspension and the reaction mixture was stirred at room temperature for 90 minutes. Once it appeared the starting material was consumed, the solvent was removed under reduced pressure to yield a yellow fluffy solid (1.1691 g, 3.44 mmol, 90% yield). The product was analyzed via NMR.

TLC: Silica gel plate, 30% EtOH/Hexanes

From bottom to top lanes: Starting material, cospot, product

Linked Entries
Attached Files
MRLS 3-1.pdf
IMG_2345.JPG
Comments
Re: Synthesis of tert-butyl (E)-3-((2-(6-chloropyrazin-2-yl)hydrazono)methyl)piperidine-1-carboxylate (MRLS 3-1) by Mandrake Fernflower
22nd September 2016 @ 22:22
Great work! Do you think it is better to couple the alcohol before the core is cyclized?
Re: Synthesis of tert-butyl (E)-3-((2-(6-chloropyrazin-2-yl)hydrazono)methyl)piperidine-1-carboxylate (MRLS 3-1) by Marco Rivas
17th October 2016 @ 19:29
Sorry! I totally missed this comment.
We already proceeded with cyclization, but this would be a cool thing to try. I have yet to give it much thought though.