tert-butyl 3-hydroxyazepane-1-carboxylate Chemical Properties

Boiling point:

310.6±35.0 °C(Predicted)

Density 

1.079±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.74±0.20(Predicted)

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C11H21NO3/c1-11(2,3)15-10(14)12-7-5-4-6-9(13)8-12/h9,13H,4-8H2,1-3H3

InChIKey

YLXNIRRSRXUTCK-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCCCC(O)C1

tert-butyl 3-hydroxyazepane-1-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl 3-hydroxyazepane-1-carboxylate from N-Boc-3-azepanone: Sodium borohydride (NaBH4) (0.98 g, 25.8 mmol) was added batchwise to a solution of N-Boc-3-azepanone (5.5 g, 25.8 mmol) in methanol (55 mL) at 0 °C, and the progress of the reaction was monitored by thin-layer chromatography (TLC). Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5 to 6 with hydrochloric acid (HCl) solution, followed by filtration and extraction with dichloromethane (DCM, 100 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to afford tert-butyl 3-hydroxyazepane-1-carboxylate (oil, 4.8 g, 87% yield). The structure of the product was confirmed by 1H NMR (400 MHz, d6-DMSO): δppm 3.95-3.93 (m, 1H), 3.71-3.62 (m, 2H), 3.40 (m, 1H), 3.32-3.28 (m, 1H), 3.03 (m, 1H), 1.88-1.65 (m, 4H), 1.55-1.36 ( m, 11H).

References

[1] Patent: US2017/313683, 2017, A1. Location in patent: Paragraph 1046-1047
[2] Patent: WO2012/80990, 2012, A1. Location in patent: Page/Page column 129-130
[3] Patent: US2012/190678, 2012, A1. Location in patent: Page/Page column 80
[4] Process Biochemistry, 2017, vol. 56, p. 90 - 97
[5] Patent: WO2018/26371, 2018, A1. Location in patent: Paragraph 0174

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