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

HRID 627093Notes

Reaction equation

HRID 627093 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[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]([CH3:18])[CH3:17])[C@H:13]([OH:19])[CH2:12][N:11]1[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852363(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-isopropyl-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 89851977(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-isopropyl-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 35, 0.667 g, 1.74 mmol) following the procedure described for Intermediate 8. The desired product was obtained as a colorless oil (0.464 g, 69%).

Sources & evidence

ORD record
ord-0b0694cfaccd41feb657f8d0507d7df3
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…