cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole Chemical Properties

Boiling point:

295.4±33.0 °C(Predicted)

Density 

1.076±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

10.72±0.20(Predicted)

form 

solid

color 

White

InChI

InChI=1/C11H20N2O2/c1-11(2,3)15-10(14)13-6-8-4-12-5-9(8)7-13/h8-9,12H,4-7H2,1-3H3/t8-,9+

InChIKey

FYUVLZRRIRGSTE-DTORHVGOSA-N

SMILES

C(N1C[C@]2([H])CNC[C@]2([H])C1)(=O)OC(C)(C)C |&1:3,8,r|

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933998090

cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole Usage And Synthesis

Uses

cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole is used as a pharmaceutical intermediate in the preparation of Bicyclic pyrazole bruton's tyrosine kinase inhibitors and anticancer active ingredients. It is also used in the synthesis of other organics , such as 6-heterocycloalkyl quinazoline derivatives.

Synthesis

General procedure for the synthesis of tert-butyl cis-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate from tert-butyl cis-5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate: To tert-butyl (5 g, 16.5 mmol)-5-benzylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (5 g), 16.5 mmol ) was added to a solution of 10% Pd(OH)2/C catalyst (0.5 g) in methanol (50 mL). The reaction mixture was subjected to a hydrogen atmosphere (60 psi) and stirred at 60 °C overnight and subsequently cooled to room temperature. The reaction mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to afford tert-butyl (3R,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate as a colorless oil (2.3 g, 66% yield).

References

[1] Patent: US2002/19388, 2002, A1
[2] Patent: WO2015/120049, 2015, A1. Location in patent: Page/Page column 139; 140
[3] Patent: WO2016/191172, 2016, A1. Location in patent: Page/Page column 86
[4] Patent: US2009/281118, 2009, A1. Location in patent: Page/Page column 10
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4126 - 4141

cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole(250275-15-1)Related Product Information

• tert-Butyl bromoacetate
• tert-Butyl acetoacetate
• tert-Butyl acrylate
• tert-Butanol
• Buprofezin
• RESMETHRIN
• 2-Butoxyethanol
• Polyvinylpyrrolidone
• Pyrrole
• Pyrrolidine
• Butyl acetate
• N-Vinyl-2-pyrrolidone
• N-Methyl-2-pyrrolidone
• tert-Butyl acetate
• Povidone iodine
• tert-Butyl carbazate
• Butyl acrylate
• cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester