Sodium Carbonate → 5-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406338Notes

Reaction equation

HRID 2406338 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH2:25][C:9]3([CH2:24][C:11]4([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[CH2:10]3)[O:8][C:5]2=[CH:6][N:7]=1.[CH3:26][S:27]([N:30]1[CH2:35][CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH2:32][CH2:31]1)(=[O:29])=[O:28].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[CH3:26][S:27]([N:30]1[CH2:31][CH:32]=[C:33]([C:2]2[CH:3]=[C:4]3[CH2:25][C:9]4([CH2:24][C:11]5([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:13][CH2:12]5)[CH2:10]4)[O:8][C:5]3=[CH:6][N:7]=2)[CH2:34][CH2:35]1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 679734971-Methanesulfonyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 867012005-Chloro-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Product 1

HCID 721948505-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-chloro-1″-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] (0.10 g), 1-methanesulfonyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine (0.10 g), 2 M aqueous Na2CO3 solution (0.37 mL), and 1,4-dioxane (2 mL) is sparged with argon for 10 min. Tetrakis(triphenylphosphine)palladium(0) (20 mg) is added and the mixture is stirred in a microwave oven at 150° C. for 1.5 h. After cooling to room temperature, water and methanol are added and the resulting mixture is filtered. The filtrate is concentrated and the residue is chromatographed on reversed phase (HPLC, methanol/water) to give the title compound. LC (method 2): tR=1.63 min; Mass spectrum (ESI+): m/z=490 [M+H]+.

Workup

  1. customis sparged with argon for 10 min
  2. additionTetrakis(triphenylphosphine)palladium(0) (20 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater and methanol are added
  5. filtrationthe resulting mixture is filtered
  6. concentrationThe filtrate is concentrated
  7. customthe residue is chromatographed on reversed phase (HPLC, methanol/water)

Sources & evidence

ORD record
ord-3e03cf9c220d44e18a794af1117b1759
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Reaction notes

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