tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylate → (2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-iodo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627105Notes

Reaction equation

HRID 627105 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([I:16])[C:13](=[O:17])[CH2:12][N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([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]([I:16])[C@H:13]([OH:17])[CH2:12][N:11]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852486tert-Butyl (3S,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-3-hydroxy-4-methyl-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 131735281(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-iodo-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate2×

Product 1

HCID 89852011(2S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-4-iodo-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-iodo-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 51, 10 g, 21.39 mmol) following the procedure described for Intermediate 8. The desired product was obtained as a colorless oil (8.87 g, 88%).

Sources & evidence

ORD record
ord-0950cae1de984bccb79cc2040b8834cf
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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