METHYL-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

268℃

Density 

1.03

Flash point:

116℃

storage temp. 

2-8°C(protect from light)

pka

9.85±0.10(Predicted)

form 

liquid

color 

Pale yellow

InChI

InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12(4)8-5-6-11-7-8/h8,11H,5-7H2,1-4H3/t8-/m1/s1

InChIKey

XYKYUXYNQDXZTD-MRVPVSSYSA-N

SMILES

C(OC(C)(C)C)(=O)N(C)[C@@H]1CCNC1

Safety Information

HS Code 

2933998090

METHYL-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of (R)-3-(N-BOC-N-methylamino)pyrrolidine from the compound (CAS: 638217-49-9): preparation of tert-butyl [(3R)-pyrrolidin-3-yl]carbamate; dissolution of carbamate of compound 46 (15.58 g, 46.6 mmol) in ethanol (150 mL) under 5% Pd/C (1 g) ) catalyzed hydrogenation at 50 psi hydrogen pressure and room temperature for 18 hours. Subsequently, Pd/C (500 mg) was added additionally and the hydrogenation was continued under the same conditions for 26 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under vacuum. Purification by column chromatography (eluent: DCM:MeOH:0.880 ammonia, volumetric ratio tapered from 100:0:0 to 90:10:1) afforded (R)-3-(N-BOC-N-methylamino)pyrrolidine as a light yellow oil (5.85 g, 62% yield).1H NMR (400 MHz, CDCl3) δ: 4.56 (1H, m) , 3.06 (2H, m), 2.87 (1H, m), 2.79 (1H, m), 2.78 (3H, s), 2.54 (1H, s), 1.95 (1H, m), 1.73 (1H, m), 1.43 (9H, s) ppm. m/z MS (ESI): 201 [M + H]+.

References

[1] Patent: US2007/185075, 2007, A1. Location in patent: Page/Page column 23-24
[2] Patent: WO2010/75270, 2010, A1. Location in patent: Page/Page column 179

METHYL-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER(392338-15-7)Related Product Information

• (R)-3-N-Boc-3-(methylamino)piperidine
• Carbamic acid, [(2R)-2-pyrrolidinylmethyl]-, 1,1-dimethylethyl ester (9CI)
• (S)-3-(Boc-amino)pyrrolidine
• METHYL-PYRROLIDIN-3-YL-CARBAMIC ACID TERT-BUTYL ESTER
• 3-(N-TERT-BUTOXYCARBONYL-N-METHYLAMINO)PYRROLIDINE
• 2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER
• N-BOC-2,5-DIAZA-BICYCLO[2.2.1]HEPTANE DITRIFLUOROACETATE