N-Boc-1-amino-cyclobutyl-methanol Chemical Properties

Boiling point:

312.2±11.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.12±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C10H19NO3/c1-9(2,3)14-8(13)11-10(7-12)5-4-6-10/h12H,4-7H2,1-3H3,(H,11,13)

InChIKey

CLRGYDRXIYIAHC-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1(CO)CCC1

Safety Information

HS Code 

2921490090

N-Boc-1-amino-cyclobutyl-methanol Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (1-(hydroxymethyl)cyclobutyl)carbamate from ethyl BOC-1-aminocyclobutanecarboxylate: at -15 °C and under nitrogen protection, lithium aluminum hydride (12.8 mL, 25.6 mmol, 2.0 M THF solution) was added slowly and dropwise to a solution of ethyl 1-((tert-butoxycarbonyl)amino)cyclobutanecarboxylate (2.97 g, 12.2 mmol) in ether (50 mL). mmol, 2.0 M THF solution), and the dropwise addition time was controlled to 40 min. The reaction mixture was maintained at -10 °C for 1.5 h. The reaction was then quenched sequentially with water (4 mL), 2N NaOH solution (5.4 mL) and additional water (11 mL). The reaction system was slowly warmed to room temperature and stirring was continued for 30 minutes. After drying by adding anhydrous magnesium sulfate, the filtrate was filtered through diatomaceous earth and the cake was washed well with ethyl acetate. The filtrate was concentrated to afford the target product, tert-butyl (1-(hydroxymethyl)cyclobutyl)carbamate, as an off-white solid (2.34 g, 95% yield).

References

[1] Patent: WO2016/179550, 2016, A1. Location in patent: Paragraph 0191

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