Dihydropyridines → Diethyl 2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-4-[6-(ethoxycarbonyl)-3-pyridazinyl]-6-(4-fluorobenzyl)-3,5-pyridinedicarboxylate

HRID 458448Notes

Reaction equation

HRID 458448 reaction equation
N1C=CC=CC1.[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]1[NH:20][C:21]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][CH:48]=2)=[C:22]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:23]([C:30]2[N:31]=[N:32][C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][CH:35]=2)[C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:13])([CH3:10])([CH3:9])[CH3:8].[N+]([O-])([O-])=O.[Ce].[NH4+]>C(#N)C.O>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][CH2:16][C@H:15]1[C:19]1[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([C:30]2[N:31]=[N:32][C:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][CH:35]=2)[C:22]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:21]([CH2:46][C:47]2[CH:48]=[CH:49][C:50]([F:53])=[CH:51][CH:52]=2)[N:20]=1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 3

HCID 407038DihydropyridinesHCID 57418452Ammonium cerium-nitrateHCID 69515611diethyl 2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-4-[6-(ethoxycarbonyl)-3-pyridazinyl]-6-(4-fluorobenzyl)-1,4-dihydro-3,5-pyridinedicarboxylate

Product 1

HCID 69516647Diethyl 2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-4-[6-(ethoxycarbonyl)-3-pyridazinyl]-6-(4-fluorobenzyl)-3,5-pyridinedicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To the dihydropyridine (D, diethyl 2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-4-[6-(ethoxycarbonyl)-3-pyridazinyl]-6-(4-fluorobenzyl)-1,4-dihydro-3,5-pyridinedicarboxylate, 265 mg, 0.41 mmol} in 9 ml acetonitrile, ammonium cerium nitrate (445 mg, 0.82 mmol) in 1.8 ml water was added. The reaction mixture was stirred for 5 minutes. Ten (10) ml water was added and then extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate. Removal of the solvent provided 260 mg orange foam which was carried to the next step without further purification. ESI-MS m/z 651 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-bae7d683ad0d426984d28d8ab85623fd
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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