Potassium Carbonate → Tert-butyl 3-(1h-indol-3-yl)piperidine-1-carboxylate

HRID 1070572Notes

Reaction equation

HRID 1070572 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1.[C:16]([O-:19])([O-])=[O:17].[K+].[K+]>CC(C)=O.O>[C:3]([O:19][C:16]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:2]1)=[O:17])([CH3:7])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 153894433-(Piperidin-3-YL)-1H-indole

Product 1

HCID 69373374Tert-butyl 3-(1h-indol-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of the 3-piperidin-3-yl-1H-indole obtained in Example 29 in acetone/water (1:1) at 0° C. is treated with di-tert-dicarbonate (4.1 g, 18.7 mmol) and K2CO3 (11.75 g, 85 mmol), stirred for 2 hours while warming to room temperature, and concentrated in vacuo. The resultant aqueous mixture is extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by column chromatography (silica gel, 1% NH4OH in MeOH:CHCl3, 0:100 to 10:90 as eluent) to afford the title product, 1.25 g, identified by HPLC and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is purified by column chromatography (silica gel, 1% NH4OH in MeOH:CHCl3, 0:100 to 10:90 as eluent)

Sources & evidence

ORD record
ord-388b73abb6634dd08566a7a2884c3a44
Source dataset
uspto-grants-2005_06
Patent number
US06903112B2

Reaction notes

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