Methyl 1-Boc-azetidine-3-carboxylate Chemical Properties

Boiling point:

269.0±33.0 °C(Predicted)

Density 

1.072 g/mL at 25 °C

refractive index 

n20/D1.452

Flash point:

>110℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

pka

-2.97±0.40(Predicted)

color 

Colorless to light yellow

InChI

InChI=1S/C10H17NO4/c1-10(2,3)15-9(13)11-5-7(6-11)8(12)14-4/h7H,5-6H2,1-4H3

InChIKey

SECFRXGVLMVUPD-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

Methyl 1-Boc-azetidine-3-carboxylate Usage And Synthesis

Uses

Building block used as a precursor to the synthesis of azaspiro[3.4]octanes developed in the Carreira group. This substrate can be readily functionalized via enolization at the 3-position in the presence of LDA.

Synthesis

General procedure for the synthesis of methyl 1-(tert-butoxycarbonyl)azetidine-3-carboxylate from methanol and 1-Boc-azetidine-3-carboxylic acid: 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (AXL016917, 1000 mg, 4.97 mmol) was dissolved in a mixture of solvents with methanol (5 mL) and toluene (20 mL), and subsequently the solution was cooled to 0°C. Trimethylsilyl diazomethane (7.45 mmol) was slowly added dropwise over a period of 15 min, during which slight bubble production was observed. The color of the solution gradually changed from clear to light yellow. The reaction mixture was continued to be stirred at 0 °C for 10 min, followed by slow warming to room temperature over a period of 30 min. Upon completion of the reaction, toluene was removed by concentration and distillation under reduced pressure to afford 1.055 g of methyl 1-(tert-butoxycarbonyl)azetidine-3-carboxylate (99% crude yield), which could be used in the next step of the reaction without further purification.

IC 50

Non-cleavable Linker

References

[1] Patent: WO2006/21881, 2006, A2. Location in patent: Page/Page column 61
[2] Patent: WO2013/83991, 2013, A1. Location in patent: Page/Page column 69
[3] Patent: WO2012/142237, 2012, A1. Location in patent: Page/Page column 98-99

Methyl 1-Boc-azetidine-3-carboxylate(610791-05-4)Related Product Information

• 1-Boc-Azetidine-3-yl-methanol
• 3-Azetidinecarboxylic acid
• Methyl 1-Boc-azetidine-3-carboxylate
• 1-N-Boc-3-Azetidinecarboxylic acid
• TERT-BUTYL 3-(METHOXYMETHYL)AZETIDINE-1-CARBOXYLATE
• azetidine-3-carboxylic acid methyl ester
• 3-FORMYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• (S)-AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER
• AZETIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER
• AZETIDINE-1,3-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 3-ETHYL ESTER