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146231-54-1

146231-54-1 Structure

146231-54-1 Structure
IdentificationBack Directory
[Name]

cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester
[CAS]

146231-54-1
[Synonyms]

2-Boc-5-oxo-hexahydrocyclopenta[c]pyrrole
(3aR,6aS)-2-Boc-5-oxohexahydrocyclopenta[c]pyrrole
tert-Butyl 5-oxo-octahydrocyclopenta-[c]pyrrole-2-carboxylate
tert-butyl cis-5-oxo-octahydrocyclopenta[c]pyrrole-2-carboxylate
cis-tert-Butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
tert-butyl (3aR,6aS)-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester
(3aR,6aS)-tert-Butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate 95+%
(3aR,6aS)-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester
(3aR,6aS)-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid 1,1-dimethylethyl ester
Cyclopenta[c]pyrrole-2(1H)-carboxylic acid, hexahydro-5-oxo-, 1,1-dimethylethyl ester, (3aR,6aS)-rel-
[Molecular Formula]

C12H19NO3
[MDL Number]

MFCD18782907
[MOL File]

146231-54-1.mol
[Molecular Weight]

225.28
Chemical PropertiesBack Directory
[Melting point ]

70-71 °C
[Boiling point ]

325.8±35.0 °C(Predicted)
[density ]

1.139±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[form ]

solid
[pka]

-0.82±0.20(Predicted)
[color ]

White to yellow
[InChI]

InChI=1/C12H19NO3/c1-12(2,3)16-11(15)13-6-8-4-10(14)5-9(8)7-13/h8-9H,4-7H2,1-3H3/t8-,9+
[InChIKey]

GGNDIMLSSMWKDR-DTORHVGONA-N
[SMILES]

C(N1C[C@]2([H])CC(C[C@]2([H])C1)=O)(=O)OC(C)(C)C |&1:3,8,r|
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester(146231-54-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

hexahydrocyclopenta[c]pyrrol-5(1H)-one

96896-09-2

cis-5-Oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylic acid tert-butyl ester

146231-54-1

Cis-hexahydrocyclopentadieno[c]pyrrol-5(1H)-one (2.0 g, 16 mmol) was used as starting material and dissolved in dichloromethane (50 mL). Subsequently, di-tert-butyl dicarbonate (5.2 g, 24 mmol), triethylamine (3.2 g, 32 mmol) and 4-dimethylaminopyridine (195 mg, 1.6 mmol) were added to the solution. The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, it was quenched by adding water (100 mL) and the aqueous and organic phases were separated. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent ratio of petroleum ether:ethyl acetate=10:1) to finally obtain tert-butyl cis-5-oxooctahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (3.4 g, 94.4% yield).

[References]

[1] Patent: US2017/112833, 2017, A1. Location in patent: Paragraph 0550-0551
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