(S)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL Chemical Properties

Boiling point:

270.3±13.0 °C(Predicted)

Density 

1.05

refractive index 

-74 ° (C=1, MeOH)

storage temp. 

2-8°C

form 

clear liquid

pka

14.77±0.10(Predicted)

color 

Colorless to Light yellow

CAS DataBase Reference

161511-85-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN2811

HS Code 

2933998090

(S)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL Usage And Synthesis

Uses

(S)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol is used for synthesis and the study of nicotinic receptor binding of PET ligand [18F]fluoroazetidinylmethoxypyridine.

Synthesis

The general procedure for the synthesis of (S)-1-(tert-butoxycarbonyl)-2-acridinemethanol from 1-Boc-L-acridine-2-carboxylic acid was as follows:Example 16 Synthesis of tert-butyl (S)-2-(hydroxymethyl)azetidine-1-carboxylate (14). To a solution of 13 (0.94 g, 4.7 mmol) in tetrahydrofuran (THF, 10 mL) was slowly added a THF solution (21.0 mL) of 1 M borane (BH3) at 0 °C. The reaction mixture was stirred at room temperature for 2 days. Subsequently, the reaction was quenched by the addition of cold water (20 mL) at 0 °C. After removal of THF by evaporation under reduced pressure, 10% aqueous citric acid solution (15 mL) was added and extracted with ethyl acetate (50 mL × 2). The combined ethyl acetate layers were washed sequentially with saturated sodium bicarbonate (NaHCO3, 30 mL) and sodium chloride (NaCl, 30 mL) aqueous solutions and dried over anhydrous sodium sulfate (Na2SO4). Ethyl acetate was removed by evaporation under reduced pressure to give 0.86 g (100% yield) of 14 as a colorless oil.1H NMR (300 MHz, CDCl3) δ 4.40 (m, 1H), 3.85-3.70 (m, 3H), 2.13 (m, 1H), 1.90 (m, 1H), 1.42 (s, 9H).

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 24, p. 7637 - 7647
[2] Patent: US2009/68105, 2009, A1. Location in patent: Page/Page column 11
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 4, p. 817 - 825
[4] Angewandte Chemie - International Edition, 2013, vol. 52, # 30, p. 7829 - 7832
[5] Angew. Chem., 2013, vol. 125, # 30, p. 7983 - 7986,4

(S)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL(161511-85-9)Related Product Information

• D-GLUCAMINE
• (R)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL
• (2S)-2-[[[5-(TRIMETHYLSTANNYL)-3-PYRIDINYL]OXY]METHYL]-1-AZETIDINECARBOXYLIC ACID, T-BUTYL ESTER
• (S)-1-(TERT-BUTOXYCARBONYL)-2-AZETIDINEMETHANOL
• 1-AZETIDINECARBOXYLIC ACID, 2-[[[2-NITRO-3-PYRIDINYL]OXY]METHYL]-, 1,1-DIMETHYLETHYL ESTER, (2S)-
• (3-[2(S)-N-(TERT-BUTOXYCARBONYL)-2-AZETIDINYL-METHOXY]PYRIDIN-2-YL)TRIMETHYLAMMONIUM TRIFLUOROMETHANESULFONATE
• 2-IODO-3-(1-TERT-BUTOXYCARBONYL-2-(S)-AZETIDINYLMETHOXY)PYRIDINE
• 1-Boc-L-azetidine-2-carboxylic acid
• (S)-N-BOC-AZETIDINE-2-CARBOXYLIC ACID METHYL ESTER