Sodium Carbonate → HCID 117849118, compound

HRID 1477637Notes

Reaction equation

HRID 1477637 reaction equation
Cl[C:2]1[N:7]=[C:6]([C@@:8]2([OH:28])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]2[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:5]=[CH:4][CH:3]=1.[CH3:29]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C(Cl)(Cl)Cl.O.O1CCOCC1>[OH:28][C@:8]1([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:29])[N:7]=2)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C@@H:9]1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 574072TrimethylboroxineHCID 117849101HCID 117849101, compound

Product 1

HCID 117849118HCID 117849118, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
88 °C

Procedure

A 1,4-dioxane (46 mL)-water (12 mL) solution of tert-butyl (3S,4S)-4-(6-chloropyridin-2-yl)-4-hydroxy-3-(pivaloyloxy)piperidine-1-carboxylate (2.30 g, 5.57 mmol) synthesized in Reference Synthesis Example 152, 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (1.2 mL, 13.4 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride-dichloromethane complex (915 mg, 1.12 mmol), and sodium carbonate (1.20 g, 11.3 mmol) was stirred under argon atmosphere at 88° C. for 3 hours. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (1.50 g, yield 69%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-da24eb7ccc3842e58ce2257a4e205348
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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