Sodium Carbonate → HCID 71208290, compound

HRID 872199Notes

Reaction equation

HRID 872199 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C@@H:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][S:25]([N:28]1[CH2:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH2:30][CH2:29]1)(=[O:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C@@H:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([C:31]4[CH2:32][CH2:33][N:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH2:29][CH:30]=4)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 86675682(R)-4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 71208290HCID 71208290, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of (R)-4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.40 g), 1-methanesulfonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine (0.38 g), 2 M aqueous Na2CO3 solution (1.3 mL), and 1,4-dioxane (8 mL) is sparged with argon for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.10 g) is added and the mixture is stirred in a microwave oven at 170° C. for 1 h. After cooling to room temperature, water is added and the resulting mixture is extracted with ethyl acetate. The combined extract is washed with brine, dried (Na2SO4), and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→0:1) to give the title compound. Mass spectrum (ESI+): m/z=464 [M+H]+.

Workup

  1. customis sparged with argon for 5 min
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.10 g) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater is added
  5. extractionthe resulting mixture is extracted with ethyl acetate
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:7→0:1)

Sources & evidence

ORD record
ord-2b827c81146b4ca78315c767cd81cc84
Source dataset
uspto-grants-2015_03
Patent number
US08975277B2

Reaction notes

Loading…