Tetrabutylammonium Fluoride → (2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627127

Reaction equation

HRID 627127 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([CH2:31][O:32][Si](C(C)(C)C)(C)C)[C:20]([CH3:40])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C@H:21]([CH2:31][OH:32])[C:20]([CH3:40])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89852556(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 89852407(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-(hydroxymethyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylateYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(2S,5R)-tert-butyl 5-(N-(allyloxy)-2-nitrophenylsulfonamido)-2-((tert-butyldimethylsilyloxy)methyl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 80, 7.05 g, 11.79 mmol) in THF (100 mL) was charged with nitrogen and cooled in an ice-bath. Tetrabutylammonium fluoride in THF (14.15 mL, 14.15 mmol) was added to the solution and stirred at rt. The reaction mixture was evaporated and the crude product was loaded onto silica and purified via flash chromatography (30-100% EA/Hexanes, 40 g column), to obtain the desired product (4.52 g, 79%) as a pale yellow foam.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe reaction mixture was evaporated
  3. custompurified via flash chromatography (30-100% EA/Hexanes, 40 g column)

Sources & evidence

ORD record
ord-a9fae5c93a9a42e2882c69ddbe1f682e
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Linked notes

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