(R)-(+)-1-Boc-3-aminopyrrolidine Chemical Properties

Melting point:

243-244°C

Boiling point:

243-244°C

Density 

1.098

refractive index 

1.4720

Flash point:

196°F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Liquid

pka

9.55±0.20(Predicted)

color 

Clear pale yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C9H18N2O2/c1-9(2,3)13-8(12)11-5-4-7(10)6-11/h7H,4-6,10H2,1-3H3/t7-/m1/s1

InChIKey

CMIBWIAICVBURI-SSDOTTSWSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC[C@@H](N)C1

CAS DataBase Reference

147081-49-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

22-41-44

Safety Statements 

26-36/37/39

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29339900

(R)-(+)-1-Boc-3-aminopyrrolidine Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(R)-(+)-1-Boc-3-aminopyrrolidine may be used to prepare:

• Descarboxamide analog and N^a-methylated analogs of 4-N-(N^ω-nitro-L-argininyl)-trans-4-amino-L-proline amide.
• Histamine 3 (H₃) receptor antagonists containing pyrrolidin-3-yl-N-methylbenzamide moiety.

Synthesis

A mixture of tert-butyl (R)-3-azido pyrrolidine-1-carboxylate (250 mg, 1.18 mmol) and Pd/C (50 mg, 10% w/w) in methanol (10 mL) was reacted with stirring at room temperature for 12 h under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford tert-butyl (R)-3-aminopyrrolidine-1-carboxylate as a colorless liquid (210 mg, 96% yield). The product was characterized by 1H NMR (600 MHz, CDCl3): δ 3.33-3.49 (m, 3H), 3.27-3.32 (m, 1H), 2.95-3.03 (m, 1H), 1.98-2.08 (m, 1H), 1.63-1.70 (m, 1H), 1.41 (s, 9H). Mass spectrometry (MS-ESI) analysis showed: m/z 131.20 [M-55]+.

References

[1] Patent: WO2016/34134, 2016, A1. Location in patent: Paragraph 00508
[2] Patent: CN105399698, 2016, A. Location in patent: Paragraph 1493-1495
[3] Patent: US2009/221565, 2009, A1. Location in patent: Page/Page column 50
[4] Advanced Synthesis and Catalysis, 2009, vol. 351, # 14-15, p. 2288 - 2294
[5] Tetrahedron, 2009, vol. 65, # 41, p. 8513 - 8523

(R)-(+)-1-Boc-3-aminopyrrolidine(147081-49-0)Related Product Information

• N-Vinyl-2-pyrrolidone
• tert-Butyl peroxyacetate
• Pyrrolidine
• Polyvinylpyrrolidone
• N-Methyl-2-pyrrolidone
• tert-Butanol
• 3-Aminopyrrolidine
• tert-Butyl acetate
• METHYL-2-PYRROLIDONE
• (2S,4R)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID
• N-Boc-trans-4-amino-L-proline methyl ester hydrochloride
• L-N-[(4'-BOC)PIPERIDINO]PROLINE
• N-Boc-4-oxo-L-Proline methyl ester
• 1-BOC-3-AMINOPYRROLIDINE,DL-3-Amino-1-N-Boc-Pyrrolidine 1-N-Boc-3-Aminopyrrolidine
• (S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine
• BOC-(+/-)-3-AMINOPYRROLIDINE
• (R)-1-Boc-3-(aminomethyl)pyrrolidine
• (R)-3-Aminopyrrolidine