Potassium Carbonate → HCID 54420265, compound

HRID 1386717Notes

Reaction equation

HRID 1386717 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=[CH2:16])[CH2:10][CH2:9]1)=O)(C)(C)C.B1C2CCCC1CCC2.C(=O)([O-])[O-].[K+].[K+].Br[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[NH:35][O:34]1>C1COCC1.CCOC(C)=O.CN(C=O)C>[NH:33]1[O:34][N:35]([CH2:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]1=2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 11117722tert-Butyl 4-(prop-2-en-1-yl)piperidine-1-carboxylateHCID 21180770HCID 21180770, compound

Product 1

HCID 54420265HCID 54420265, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-t-butoxycarbonyl-4-(prop-2-enyl)piperidine (330 mg, 1.46 mmol, from EXAMPLE 33, Step B) in 0.5 mL dry THF was cooled to 0° C. and a solution of 9-BBN (3.2 mL, 0.5 M in THF, 1.61 mmol) was added. The mixture was warmed to rt and stirred for 5 h. Potassium carbonate (405 mg, 2.93 mmol), 1,2-bis(diphenylphosphino) ferrocenyl palladium dichloride (60 mg, 0.073 mmol) and 3-bromobenzofurazan (292 mg, 1.46 mmol, from EXAMPLE 33, Step C) were added followed by 5 mL of dry DMF. The resulting mixture was heated to 55° C. overnight then diluted with 50 mL EtOAc. The solution was washed with H2O (3×) and sat'd NaCl then dried over Na2SO4 and concentrated. Flash chromatography (15 g silica, 5:1 v/v hexane/EtOAc eluant) afforded the 1-t-butoxycarbonyl derivative of the title compound. Heating in 1% conc. HCl/MeOH at 50° C. for 2h followed by removal of solvent and drying under vacuum afforded 155 mg (38%) of the title compound: 1H NMR (300 MHz, CD3OD) δ 1.31-1.42 (m, 4H), 1.6-1.75 (m, 1H), 1.842.0 (m, 4H), 2.9-3.1 (m, 4H), 3.3-3.4 (m, 2H), 7.25-7.3 (d, 1H), 7.47.5 (dd, 11), 7.7-7.75 (d, 1H).

Workup

  1. temperatureThe resulting mixture was heated to 55° C. overnight
  2. washThe solution was washed with H2O (3×)
  3. dry with materialthen dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ec64560a974e47b4a7c2693bb97d8dbd
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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