ChemicalBook CAS DataBase List (3aR,6aS)-benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

(3aR,6aS)-benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate synthesis

5synthesis methods

Product Name:(3aR,6aS)-benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate
CAS Number:1217315-21-3
Molecular formula:C15H17NO3
Molecular Weight:259.3

61117-58-6 Synthesis

Cobalt, octacarbonyldi-, (Co-Co), stereoisomer

61117-58-6
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Carbamic acid, N-2-propen-1-yl-N-2-propyn-1-yl-, phenylmethyl ester

144734-57-6
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(3aR,6aS)-benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

1217315-21-3
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Yield:1217315-21-3 73%

Reaction Conditions:

in 1,2-dimethoxyethane;hexane;water at 0 - 100; for 3 h;

Steps:

1.3 Step-3: Preparation of benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(lH)-carboxylate

Step-3: Preparation of benzyl 5-oxohexahydrocyclopenta[c]pyrrole-2(lH)-carboxylate H Cbz-N^ ^=0 H [0118] To a stirred solution of benzyl allyl(prop-2-yn-l-yl)carbamate (40 g, 174.4 mmol) in a mixture of water and dimethoxy ethane (65 mL: 400 mL) was added dicobalt octacarbonyl [moistened with hexane (hexane 1-10%), > 90% (Co)] (72 g, 191.9 mmol) at 0 °C. The reaction mixture was allowed to warm to room temperature slowly and heated to 100 °C and stirred for 3 h. After completion of reaction (monitored by TLC), the reaction mixture was concentrated to afford crude product which was purified by silica gel column chromatography (50% ethylacetate/hexane) to obtain the title compound benzyl 5- oxohexahydrocyclopenta[c]pyrrole-2(lH)-carboxylate (33 g, 73 % yield) as a brown solid. Calculated (M+H): 260.12; Found (M+H): 260.2.

References:

WO2015/48507,2015,A1 Location in patent:Paragraph 0118