Sodium Carbonate → t-Butyl (1-t-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)phenylcarbamate

HRID 1419568Notes

Reaction equation

HRID 1419568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11](OS(C(F)(F)F)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)=[O:28])([CH3:25])([CH3:24])[CH3:23].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([N:29]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:27](=[O:28])[O:26][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 2773226(2-BOC-aminophenyl)boronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 53951936t-Butyl (1-t-Butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)phenylcarbamate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0) (100 mg) was added to a degassed mixture of 1-t-butoxycarbonyl-4-trifluoromethanesulfonyloxy-1,2,3,6-tetrahydropyridine (5.0 g), 2-(t-butoxycarbonylamino)phenylboronic acid (Tetrahedron Lett. 1993, 28, 5093) (4.99 g), lithium chloride (1.94 g) and aqueous sodium carbonate (2N, 21 mL) in 1,2-dimethoxyethane (100 mL). The resulting solution was heated under reflux for 3 h., cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium carbonate (2M) and the organic layer was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by MPLC on silica gel, eluting with EtOAc/Hexane (5:95) to give the title compound as a waxy solid (2.7 g), δH (CDCl3) 1.43 (18H, s), 2.29 (2H, m), 3.57 (2H, t, J 8.0 Hz), 4.00 (2H, m), 5.64 (1H, br s), 6.46 (1H, br s), 6.92-6.96 (2H, m), 7.15-7.19 (1H, m), 7.87 (1H, m).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 3 h.
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium carbonate (2M)
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by MPLC on silica gel
  9. washeluting with EtOAc/Hexane (5:95)

Sources & evidence

ORD record
ord-e57c5cb139bf4fa18c348093ed7d6ae4
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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