D-1-N-BOC-PROLINAMIDE Chemical Properties

Melting point:

100-102 °C

Boiling point:

370.1±31.0 °C(Predicted)

Density 

1.155±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

15.97±0.20(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

70138-72-6(CAS DataBase Reference)

D-1-N-BOC-PROLINAMIDE Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (R)-2-carbamoylpyrrolidine-1-carboxylate from Boc-D-proline: Example 1; Synthesis of tert-butyl (R)-2-carbamoylpyrrolidine-1-carboxylate. N-Methylmorpholine (9.85 g, 97.5 mmol) and isobutyl chloroformate (13.3 g, 97.5 mmol) were added to a THF solution (98 mL) of (R)-pyrrolidine-1,2-dicarboxylic acid 1- tert-butyl ester (20.0 g, 92.9 mmol) at -78 °C and stirred for 1 hour. Ammonium hydroxide (58 mL) was slowly added while the reaction system was warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction mixture was partitioned between dichloromethane and water. The organic phase was washed with 1 M HCl, dried over anhydrous sodium sulfate, filtered and concentrated to give the title product (10.8 g, 54%) as a colorless semi-solid.1H NMR (300 MHz, CDCl3): δ (ppm) 5.91-6.13 (m, 1H), 4.17-4.30 (m, 2H), 3.37-3.48 (m, 2H), 2.10- 2.18 (m, 2H), 1.84-1.96 (m, 2H), 1.45 (s, 9H).

References

[1] Patent: US2007/259926, 2007, A1. Location in patent: Page/Page column 9
[2] Tetrahedron, 2009, vol. 65, # 46, p. 9536 - 9541

D-1-N-BOC-PROLINAMIDE(70138-72-6)Related Product Information

• D-1-N-Boc-prolinamide
• D-Prolinamide