N-BOC-4-METHYL-4-HYDROXY PIPERIDINE Chemical Properties

Boiling point:

296.4±33.0 °C(Predicted)

Density 

1.075±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.87±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C11H21NO3/c1-10(2,3)15-9(13)12-7-5-11(4,14)6-8-12/h14H,5-8H2,1-4H3

InChIKey

SWUCHJAQBNXPBO-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(O)(C)CC1

N-BOC-4-METHYL-4-HYDROXY PIPERIDINE Usage And Synthesis

Chemical Properties

White powder, stable at room temperature and pressure, avoid contact with strong oxidants.

Synthesis

a) N-Boc-4-piperidone (1.0 g, 5.0 mmol) was dissolved in anhydrous ether (10 mL) and cooled to -10°C under nitrogen protection. An ether solution of methylmagnesium bromide (3M, 2.5 mL, 7.5 mmol) was slowly added dropwise, and the reaction mixture was stirred for 5 minutes after the drop was completed. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (10 mL) and subsequently diluted with water (20 mL) and ether (20 mL). The aqueous phase was separated and extracted with ether (2 x 30 mL), and the combined organic phases were washed with brine (50 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford N-BOC-4-methyl-4-hydroxypiperidine as a colorless oil (1.05 g, 97% yield).1H NMR (400 MHz, CDCl3) δ 3.76-3.64 (m, 2H), 3.29 -3.16 (m, 2H), 1.66 (s, 1H), 1.45 (s, 9H), 1.25 (s, 3H), solvent peaks were not clearly attributed.

References

[1] Journal of the American Chemical Society, 2013, vol. 135, # 41, p. 15342 - 15345
[2] Patent: WO2014/128465, 2014, A1. Location in patent: Page/Page column 156
[3] Patent: WO2009/151598, 2009, A1. Location in patent: Page/Page column 148-149
[4] Patent: WO2014/164409, 2014, A1. Location in patent: Page/Page column 32; 33
[5] Patent: WO2014/164428, 2014, A1. Location in patent: Page/Page column 25

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