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

HRID 557440Notes

Reaction equation

[C:1]([C:3]1[CH:4]([C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[O:25][C:24]([CH3:27])=[CH:23][C:22]3=[O:28])[C:5]([C:11]([O:13][CH2:14][CH2:15][CH3:16])=[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:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[O:25][C:24]([CH3:27])=[CH:23][C:22]3=[O:28])[C:5]([C:11]([O:13][CH2:14][CH2:15][CH3:16])=[O:12])=[C:6]([CH3:10])[NH:7][C:8]=1[CH3:9])#[N:2]

Participants

Reactant 3

HCID 8021Diethylamine

HCID 15978970Propyl 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 66991979Propyl (4S)-5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Procedure

430 mg (1.13 mmol) of racemic propyl 5-cyano-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate (example 4) are separated into the enantiomers by preparative HPLC on a chiral phase [column: Chiralpak AD-H, 250 mm×4.6 mm; eluent: isohexane/ethanol 3:1 (v/v)+0.2% diethylamine; flow rate: 1 ml/min; UV detection: 220 nm]:

Sources & evidence

ORD record: ord-28b1b3b55e15489caabb634ff59bfff8
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058447B2

Reaction notes

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