Diethylamine → Ethyl (4S)-5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 557439Notes

Reaction equation

[C:1]([C:3]1[CH:4]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[O:24][C:23]([CH3:26])=[CH:22][C:21]3=[O:27])[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([CH3:10])[NH:7][C:8]=1[CH3:9])#[N:2].CCCC(C)C.C(O)C.C(NCC)C>>[C:1]([C:3]1[C@@H:4]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[O:24][C:23]([CH3:26])=[CH:22][C:21]3=[O:27])[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:6]([CH3:10])[NH:7][C:8]=1[CH3:9])#[N:2]

Participants

Reactant 3

HCID 8021Diethylamine

HCID 15979088Ethyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HCID 86593186Isohexane ethanol

Product 1

HCID 66991510Ethyl (4S)-5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Procedure

536 mg (1.45 mmol) of racemic ethyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate (example 7) are separated into the enantiomers by preparative HPLC on a chiral phase [column: Chiralpak AS-H, 250 mm×4.6 mm; eluent: isohexane/ethanol 3:1 (v/v)+0.2% diethylamine; flow rate: 1 ml/min; W detection: 220 nm]:

Sources & evidence

ORD record: ord-00a6e586e8014570ad7cb181be0ed00e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058447B2

Reaction notes

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