Hydrochloric Acid → (3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acid

HRID 627163Notes

Reaction equation

HRID 627163 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:15]=[C:14]([C:16]([O:18]C)=[O:17])[C@H:13]([OH:20])[CH2:12][N:11]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O.[Li+].[OH-].Cl>C1COCC1>[C:24]([O:23][C:21]([N:11]1[C@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3])[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C@H:13]([OH:20])[CH2:12]1)=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 89852366(2S,5S)-1-tert-butyl 4-methyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1,4(2H)-dicarboxylate2×

Product 1

HCID 89851992(3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2S,5S)-1-tert-butyl 4-methyl 2-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-5,6-dihydropyridine-1,4(2H)-dicarboxylate (Intermediate 101, 4.22 g, 10.51 mmol) was dissolved in THF (64.0 mL) and water (32 mL) and then LiOH (0.277 g, 11.56 mmol) was added and stirred at rt overnight. The reaction mixture was acidified with 1N HCl, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated to obtain the desired product (4.07 g, 100%) as a transparent oil.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-021a7036fc644c588ea7380708a45a70
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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