(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627132Notes

Reaction equation

HRID 627132 reaction equation
[Si](OC[C@@H]1C(C)=CC(=O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C.[Si:25]([O:32][CH2:33][C@H:34]1[N:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:38][C:37]([O:47][Si](C)(C)C)=[CH:36][CH:35]1[CH:52]([CH3:54])[CH3:53])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>>[Si:25]([O:32][CH2:33][C@@H:34]1[C:35]([CH:52]([CH3:54])[CH3:53])=[CH:36][C:37](=[O:47])[CH2:38][N:39]1[C:40]([O:42][C:43]([CH3:45])([CH3:44])[CH3:46])=[O:41])([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 89852188(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylateHCID 89852312(6S)-tert-butyl 6-((tert-butyldimethylsilyloxy)methyl)-5-isopropyl-3-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89851363(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylateYield 14.32%

Procedure

(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (804 mg, 14.32%) (over two steps) was prepared as described in Intermediate 78 as a yellow oil, using (6S)-tert-butyl 6-((tert-butyldimethylsilyloxy)methyl)-5-isopropyl-3-(trimethylsilyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 88, theoretically 6.7 g, 14.64 mmol).

Sources & evidence

ORD record
ord-6fc4327e32684d569932c0cac67f0a57
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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