TERT-BUTYL (3-IODOPROPYL)CARBAMATE Chemical Properties

Melting point:

37-40 °C

Boiling point:

299.3±23.0 °C(Predicted)

Density 

1.486±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

12.54±0.46(Predicted)

color 

Pale Yellow

Safety Information

HS Code 

2921199990

TERT-BUTYL (3-IODOPROPYL)CARBAMATE Usage And Synthesis

Uses

1,1-Dimethylethyl Ester N-(3-Iodopropyl)carbamic Acid is used in preparation of isoindolin-2-one-linked quinazoline and pyridopyrimidine as Ras protein degraders and anticancer agents.

Synthesis

General procedure for the synthesis of tert-butyl (3-iodopropyl) carbamate from tert-butyl N-(3-hydroxypropyl) carbamate: firstly, 3-amino-1-propanol (3.22 mL, 40 mmol) was dissolved in 50 mL of dichloromethane (CH2Cl2), triethylamine (Et3N, 5.6 mL, 40 mmol) was added, and stirred for 30 min. Subsequently, a solution of pre-dissolved di-tert-butyl dicarbonate (Boc2O, 9.6 g, 44 mmol) in 50 mL of CH2Cl2 was slowly added and the reaction mixture was stirred at room temperature for 14 hours. After completion of the reaction, saturated aqueous ammonium chloride solution (30 mL) was added and the mixture was extracted with CH2Cl2 (3 x 20 mL). The organic phases were combined, dried and concentrated to give the crude product (6.00 g, 86% yield), which was used directly in the next step of the reaction. Next, 1H-imidazole (1.4 g, 20.57 mmol) and triphenylphosphine (5.39 g, 20.57 mmol) were dissolved in 100 mL of CH2Cl2 and cooled to 0 °C before adding iodine (I2, 5.22 g, 20.57 mmol) in small portions. Then, a solution of the crude product (3.0 g, 17.14 mmol) obtained in the previous step dissolved in 20 mL CH2Cl2 was added. The reaction mixture was stirred for 3 h at room temperature and then poured into water (100 mL) and extracted with CH2Cl2 (50 mL). The organic phase was washed sequentially with water, 10% hydrochloric acid solution (12 mL), then extracted with CH2Cl2 (3 x 50 mL), dried and concentrated. Finally, the target product tert-butyl (3-iodopropyl)carbamate (3.78 g, 78% yield) was purified by fast chromatography (silica gel, 15% ethyl acetate/petroleum ether) as a light yellow oil.

References

[1] Journal of Organic Chemistry, 2009, vol. 74, # 17, p. 6792 - 6796
[2] Journal of Organic Chemistry, 2009, vol. 74, # 20, p. 7982 - 7985
[3] Helvetica Chimica Acta, 2002, vol. 85, # 6, p. 1659 - 1673
[4] Helvetica Chimica Acta, 2003, vol. 86, # 1, p. 233 - 246
[5] Angewandte Chemie - International Edition, 2011, vol. 50, # 23, p. 5379 - 5382

TERT-BUTYL (3-IODOPROPYL)CARBAMATE(167479-01-8)Related Product Information

• 3(S)-IODOMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• TERT-BUTYL (3-IODOPROPYL)CARBAMATE
• N-Boc-4-iodopiperidine
• BOC-TRANS-4-IODO-L-PROLINE
• tert-Butyl 3-(iodomethyl)pyrrolidine-1-carboxylate
• N-BOC-TRANS-4-IODO-L-PROLINE METHYL ESTER
• TERT-BUTYL 3-(IODOMETHYL)AZETIDINE-1-CARBOXYLATE
• 3(R)-IODOMETHYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
• 1-N-BOC-3-IODOMETHYLPIPERIDINE