(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate → (2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627271Notes

Reaction equation

HRID 627271 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH:16]2[CH2:18][CH2:17]2)[C:13](=[O:19])[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H]1C=C(C)[C@H](O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C>>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH:16]2[CH2:18][CH2:17]2)[C@H:13]([OH:19])[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852228(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate2×HCID 89852486tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 89852220(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 263, 3.82 g, 10.01 mmol) following the procedure described for Intermediate 8. The desired product was obtained as a colorless oil (3 g, 78%).

Sources & evidence

ORD record
ord-6d0893a44e0249a999cf5056fae6daf5
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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