| Identification | Back Directory | [Name]
cis-2-Boc-hexahydropyrrolo[3,4-c]pyrrole | [CAS]
250275-15-1 | [Synonyms]
4-c]pyrrole
cis-2-Boc-hexahydropyrrolo[3
-Boc-hexahydropyrrolo[3,4-c]pyrrole
3-Boc-3,7-diazabicyclo[3.3.0]octane
Cis-2-Boc-hexahydropyrrol-3,4-cpyrrole
cis-3-Boc-3,7-diazabicyclo[3.3.0]octane
CIS-2-BOC-HEXAHYDROPYRROLO[3,4-C]PYRROLE
2-boc-hexahydropyrrolo[3,4-c]pyrrole, cis
cis-3,7-Diazabicyclo[3.3.0]octane, N3-BOC protected
2-(tert-Butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrole
cis-2-(tert-Butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrole
tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
tert-butyl cis-octahydropyrrolo[3,4-c]pyrrole-2-carboxylate
cis-tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
tert-Butyl cis-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
meso-tert-Butyl hexahydropyrrolo-[3,4-c]pyrrole-2(1H)-carboxylate
Racemiccis-Tertbutylhexahydropyrrolo[3,4-c]Pyrrole-2(1H)-Carboxylate
(3aR,6aS)-tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
tert-Butyl (3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
(3aR,6aS)-tert-butyl 3a,6a-diMethylhexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate
tert-butyl (3aR,6aS)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carboxylate
CIS-tert-butyl (3aR,6aS)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrole-5-carboxylate
Pyrrolo[3,4-c]pyrrole-2(1H)-carboxylicacid, hexahydro-, 1,1-diMethylethyl ester, (3aR,6aS)-rel-
tert-Butyl cis-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, cis-Octahydropyrrolo[3,4-c]pyrrole, N2-BOC protected | [Molecular Formula]
C11H20N2O2 | [MDL Number]
MFCD04116224 | [MOL File]
250275-15-1.mol | [Molecular Weight]
212.29 |
| Chemical Properties | Back Directory | [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 | [form ]
solid | [pka]
10.72±0.20(Predicted) | [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| |
| Hazard Information | Back Directory | [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 |
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