tert-Butyl 6-methylpiperidin-3-ylcarbamate Chemical Properties

Density 

1.00

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Light yellow to brown Liquid

InChI

InChI=1S/C11H22N2O2/c1-8-5-6-9(7-12-8)13-10(14)15-11(2,3)4/h8-9,12H,5-7H2,1-4H3,(H,13,14)

InChIKey

NNMBHCRWGGSRBE-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1CCC(C)NC1

Safety Information

HS Code 

2933599590

tert-Butyl 6-methylpiperidin-3-ylcarbamate Usage And Synthesis

Synthesis

Step 2. Synthesis of racemic-cis/trans-tert-butyl (6-methylpiperidin-3-yl) carbamate. Platinum(II) oxide (2.5 g) was added to a dry hydrogenation flask under argon protection. Subsequently, a solution of N-Boc-6-methyl-3-aminopyridine (33 g, 158.5 mmol) in acetic acid (300 mL) was added, and the resulting mixture was hydrogenated at 50 °C under 55 psi hydrogen pressure for 30 hours. The reaction was monitored by thin layer chromatography (TLC) (petroleum ether/ethyl acetate, 2:1) to confirm complete consumption of the feedstock. The reaction mixture was filtered and the filter cake was washed with methanol (50 mL x 2). The combined filtrates were concentrated under reduced pressure to afford tert-butyl (6-methylpiperidin-3-yl) carbamate (34 g, 100%) as a yellow oil (cis/trans ratio 2:1), which could be used in the subsequent steps without further purification.LC/MS analysis showed (M+H)+ of 215.2.

References

[1] Patent: US2015/158864, 2015, A1. Location in patent: Paragraph 0270
[2] Patent: WO2010/16005, 2010, A1. Location in patent: Page/Page column 135-136
[3] Patent: WO2016/196776, 2016, A2. Location in patent: Paragraph 001090
[4] Patent: WO2012/148775, 2012, A1. Location in patent: Page/Page column 114

tert-Butyl 6-methylpiperidin-3-ylcarbamate(1150618-39-5)Related Product Information

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