Reacción #58774

ord-bbd7d798654d40d2a16d1a5d7de0ddf3

Ecuación de reacción

CN(C)C(N(C)C)N(C)C
tris(dimethylamino)methane
CCOC(=O)C1=C(C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
compound ( 23 )
CCOC(=O)C1=C(C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
(S)-5-diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester
CCC(=O)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)(C)c1ccccc1
example 17
CCC(=O)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)(C)c1ccccc1
2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
→
CCOC(=O)C1=C(/C=C/N(C)C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
crude product
CCOC(=O)C1=C(/C=C/N(C)C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
(S)-5-diethylcarbamoyl-4-((E)-2-dimethylamino-vinyl)-5-ethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester

Reactantes

CN(C)C(N(C)C)N(C)C
tris(dimethylamino)methane
—
Example 6 1.22
CCOC(=O)C1=C(C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
compound ( 23 )
CCOC(=O)C1=C(C)[C@@](CC)(C(=O)N(CC)CC)OC1=O
(S)-5-diethylcarbamoyl-5-ethyl-4-methyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid ethyl ester
CCC(=O)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)(C)c1ccccc1
example 17
CCC(=O)C(=O)O[C@@H]1C[C@H](C)CC[C@H]1C(C)(C)c1ccccc1
2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethyl formamide

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

According to the procedure described in Example 6 1.22 0 g of compound (23) as obtained from example 17 (4.103 mmol) in 7.3 mL dimethyl formamide were treated with 7.55 mL tris(dimethylamino)methane (42.26 mmol, 10.3 eq) yielding the crude product as an orange oil (1.463 mg, 101% by weight).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07423152B2uspto-grants-2008_09