Water → HCID 59808495, compound

HRID 1942509Notes

Reaction equation

HRID 1942509 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].[C:7]1([C:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)Cl.[OH2:29]>C(O)(C)(C)C.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[Fe+3].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1>[OH:29][C@H:18]1[C@:13]([OH:2])([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17]1

Participants

8

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 15442738tert-Butyl 4-phenyl-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59808495HCID 59808495, compound

Reagents, catalysts & solvents 3

HCID 26250Potassium ferricyanideCatalystHCID 112172021,4-Bis(dihydroquinidine)phthalazineCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of potassium osmate (VI) 2 hydrate (8.0 g), (DHQD)2PHAL (14.2 g), potassium carbonate (379 g), potassium hexacyanoferrate (III) (903 g) in t-butanol (4.8 L) and water (4.8 L) was added methenesulfonamide (73.4 g) at room temperature. Then, tert-butyl 4-phenyl-3,6-dihydropyridine-1(2H)-carboxylate (200 g) was added thereto in an ice-bath, and the mixture was stirred for 2 hours. The mixture was further stirred at room temperature for 12 hours, and thereto was added methylene chloride (7.0 L) for separation to give the organic layer. The aqueous layer was washed twice with methylene chloride, and the obtained organic layers were combined, washed with 2M aqueous potassium hydroxide solution, dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (215.5 g).

Workup

  1. stirringThe mixture was further stirred at room temperature for 12 hours
  2. customfor separation
  3. customto give the organic layer
  4. washThe aqueous layer was washed twice with methylene chloride
  5. washwashed with 2M aqueous potassium hydroxide solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4797e5e7d8f54dda9945dfbe1f2bfe92
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

Loading…