Triethylamine → tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate

HRID 1853034Notes

Reaction equation

HRID 1853034 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][BH:24][O:23]1.C(N(CC)CC)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O1CCOCC1>[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][B:24]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[O:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 272817821-N-Boc-4-(4-bromophenyl)piperidine

Product 1

HCID 53629760tert-Butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylateYield 59.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of tert-butyl 4-(4-bromophenyl)piperidine-1-carboxylate (13.5 g, 39.7 mmol) in dioxane (40 mL) was added 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.64 mL, 59.5 mmol) and triethylamine (16.6 mL, 119 mmol). The solution was purged with argon for 5 minutes. Dichlorobis(acetonitrile) palladium (0.309 g, 1.19 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.95 g, 4.76 mmol) were then added, and the reaction mixture was again purged with argon for 5 minutes. The reaction mixture was then sealed and heated at 110° C. for 90 minutes. The reaction mixture was cooled to ambient temperature and filtered through a glass fiber filter paper. The filtrate was concentrated under reduced pressure and the residue purified by silica gel column chromatography, eluting with 5-10% EtOAc in hexanes to afford tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine-1-carboxylate (9.13 g, 23.6 mmol, 59.4% yield) as a solid. MS (apci) m/z=288.3 (M+H-Boc).

Workup

  1. customThe solution was purged with argon for 5 minutes
  2. customthe reaction mixture was again purged with argon for 5 minutes
  3. customThe reaction mixture was then sealed
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. filtrationfiltered through a glass fiber
  6. filtrationfilter paper
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue purified by silica gel column chromatography
  9. washeluting with 5-10% EtOAc in hexanes

Sources & evidence

ORD record
ord-22811cd10aa44fedab190626372eec47
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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