Triethylamine → HCID 66876110, compound

HRID 1666525Notes

Reaction equation

HRID 1666525 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=1)[CH:16]=[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:12][C:13]2[CH:14]=[C:15]([CH:30]=[CH:31][CH:32]=2)[CH:16]=[C:17]2[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[O:24])[CH2:21][CH2:22]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 201262(4-Methoxyphenyl)boronic acidHCID 53485958Tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate

Product 1

HCID 66876110HCID 66876110, compoundYield 32.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-methoxyphenylboronic acid (1.57 g, 10.36 mmole) and tert-butyl 4-(3-hydroxybenzylidene)piperidine-1-carboxylate (2.5 g, 8.6 mmole) in dichloromethane (75 mL) were added copper acetate (1.63 g, 8.6 mmole), triethyl amine (5.219 g, 51.6 mmol) and molecular sieves. The mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite pad. The filtrate was evaporated and purified by column chromatography to give the title compound (1.1 g, 32%). 1H NMR (500 MHz, CDCl3): δ ppm 7.26 (t, 1H), 6.99 (d, 2H), 6.89 (t, 3H), 6.79 (t, 2H), 6.29 (s, 1H), 3.80 (s, 3H), 3.48 (s, 2H), 3.38 (s, 2H), 2.42 (s, 2H), 2.29 (s, 2H), 1.47 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through celite pad
  2. customThe filtrate was evaporated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-71a7903e805d45c59037bb8ff80871b0
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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