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

HRID 627164Notes

Reaction equation

HRID 627164 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:12]=[C:11]([C:23](O)=[O:24])[C@H:10]([OH:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][NH:28][CH3:29].C1COCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Si:16]([O:15][CH2:14][C@@H:13]1[CH:12]=[C:11]([C:23](=[O:24])[N:28]([CH3:29])[CH3:27])[C@H:10]([OH:26])[CH2:9][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89851992(3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acid2×

Product 1

HCID 89851842(2S,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(dimethylcarbamoyl)-5-hydroxy-5,6-dihydropyridine-1 (2H)-carboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S,6S)-1-(tert-butoxycarbonyl)-6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-1,2,3,6-tetrahydropyridine-4-carboxylic acid (Intermediate 136, 4.07 g, 10.50 mmol) in DMF (20 mL) at room temperature was added 2M dimethylamine in THF (5.25 mL, 10.50 mmol), HATU (5.99 g, 15.75 mmol) and then DIEA (5.50 mL, 31.51 mmol). The reaction mixture was stirred at room temperature. The reaction ran until the starting material was consumed, then it was quenched with water and extracted with EtOAc. The organic solutions was then washed with brine, and purified via flash chromatography (35-100% EA/Hex) to isolate the desired product (3.05 g, 70.0%) as a pink glassy solid.

Workup

  1. customwas consumed
  2. customit was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organic solutions was then washed with brine
  5. custompurified via flash chromatography (35-100% EA/Hex)

Sources & evidence

ORD record
ord-10f70fc317eb48e690644e7ed846fffe
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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