ChemicalBook CAS DataBase List (1R,5S,6r)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

(1R,5S,6r)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate synthesis

6synthesis methods

Product Name:(1R,5S,6r)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate
CAS Number:146726-10-5
Molecular formula:C16H19NO4
Molecular Weight:289.33

31970-04-4 Synthesis

31970-04-4
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(1R,5S,6s)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

134575-38-5
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(1R,5S,6r)-3-benzyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

146726-10-5
4 suppliers
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Yield:146726-10-5 28% ，134575-38-5 57%

Reaction Conditions:

rhodium(II) acetate in hexane;dichloromethane;ethyl acetate;

Steps:

L [1α,5α,6β]-3-Benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid, ethyl ester

[1α,5α,6β]-3-Benzyloxycarbonyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid, ethyl ester A solution of ethyl diazoacatate (5.8 ml, 55 mmol) in methylene chloride (32 ml) was added slowly (over 70 hours, using a syringe pump) to a mixture of 1-benzyloxycarbonyl-3-pyrroline (9.25 g, 50.0 mmol), and rhodium acetate (1.0 g, 2.3 mmol) in methylene chloride (140 ml). At the end of the addition, the reaction mixture was filtered through Celite and concentrated in vacuo . The residue was purified by column chromatography (eluant: 10% ethyl acetate in hexane) to provide recovered starting material (3.2 g, 17.3 mmol) and the title products: [1α,5α,6α]-3-Benzyloxycarbonyl-3-azabicyclo[3.1.0] hexane-6-carboxylic acid, ethyl ester: (2.61 g, 9.02 mmol, 28% yield based on recovered starting material): ¹H NMR (CDCl₃): 7.32 (m, 5H), 5.08 (s, 2H), 4.10 (q, J=7.4 Hz, 2H), 3.71 (dd, J=14, 11.4 Hz, 2H), 3.49 (m, 2H), 2.07 (m, 2H), 1. (m, 1H), 1.23 (t, J=7.4 Hz, 3H). [1α,5α,6β]-3-Benzyloxycarbonyl-3-azabicyclo[3.1.0] hexane-6-carboxylic acid, ethyl ester: (5.4 g, 18.7 mmol, 57% yield based on recovered starting material): ¹H NMR (CDCl₃): 7.30 (m, 5H), 5.06 (s, 2H), 3.97 (q, J=7 Hz, 2H), 3.80 (d, J=11.2 Hz, 2H), 3.49 (m, 2H), 1.87 (m, 2H), 1.75 (m, 1H), 1.12 (t, J=7 Hz, 3H).

References:

EP413455,1991,A2