(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((4-methoxybenzyl)-oxy)methyl)-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate → (2S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-4-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627190Notes

Reaction equation

HRID 627190 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:13](=[O:27])[CH2:12][N:11]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([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]([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:13]([OH:27])[CH2:12][N:11]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852314(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((4-methoxybenzyl)-oxy)methyl)-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 131735286(2S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-hydroxy-4-(((4-methoxybenzyl)oxy)methyl)-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(((4-methoxybenzyl)oxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 168, 34.99 mmol) according to the procedure for Intermediate 8. The reaction mixture was concentrated and the white solid was redissolved in 200 mL EtOAc and washed with satd. NaHCO3, brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel column eluting with 0-100% ethyl acetate/hexanes to afford a colorless oil. 17.10 g, 99% over 2 steps.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe white solid was redissolved in 200 mL EtOAc
  3. washwashed with satd
  4. dry with materialNaHCO3, brine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column
  8. washeluting with 0-100% ethyl acetate/hexanes
  9. customto afford a colorless oil

Sources & evidence

ORD record
ord-81bcfdc5ca344567a84344599596754b
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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