1,2-Dimethoxyethane → 4-(2-Bromo-5-methoxybenzylidene)-1-Boc-piperidine

HRID 1006054Notes

Reaction equation

HRID 1006054 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:5]=1[CH2:6]P(=O)(OCC)OCC.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].COCCOC>O>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][C:31](=[CH:6][C:5]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:4]=2[Br:3])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 22675346Diethyl 2-bromo-5-methoxybenzylphosphonate

Product 1

HCID 226754064-(2-Bromo-5-methoxybenzylidene)-1-Boc-piperidineYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in paraffin, 14.4 g, 0.360 mol) was added in small portions to a mixture of the crude product (147 g) of diethyl 2-bromo-5-methoxybenzylphosphonate, N-tert-butoxycarbonyl-4-piperidone (65.1 g, 0.327 mol) and 1,2-dimethoxyethane (200 mL) at room temperature, and the resulting mixture was stirred as it was for 1.5 hours. Water (1200 mL) was added to the reaction mixture, followed by extraction with ether (500 mL×3). The combined organic layer was washed with water (200 mL) and a saturated aqueous sodium chloride solution (200 mL). The combined organic layer washed was dried over anhydrous magnesium sulfate and then concentrated to dryness, and the residue was washed with hexane to obtain 98.2 g (0.257 mol, 79%) of N-tert-butoxycarbonyl-4-(2-bromo-5-methoxybenzal)piperidine.

Workup

  1. extractionfollowed by extraction with ether (500 mL×3)
  2. washThe combined organic layer was washed with water (200 mL)
  3. washThe combined organic layer washed
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness
  6. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-64f171f829ce4297b22bdc78dd781126
Source dataset
uspto-grants-2004_09
Patent number
US06787560B2

Reaction notes

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