Reaktion #58774

ord-bbd7d798654d40d2a16d1a5d7de0ddf3

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethyl formamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07423152B2uspto-grants-2008_09