Potassium Carbonate → HCID 118365325, compound

HRID 588168Notes

Reaction equation

HRID 588168 reaction equation
Br[CH2:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[F:11].[C:12]([O:16][C:17]([NH:19][C@@H:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH3:10])[C:3]=1[CH2:2][N:22]1[CH2:23][CH2:24][CH2:25][C@@H:20]([NH:19][C:17](=[O:18])[O:16][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:21]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protectedHCID 27793222-Fluoro-6-methoxybenzyl bromide

Product 1

HCID 118365325HCID 118365325, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Bromomethyl)-1-fluoro-3-methoxybenzene (3.19 g, 14.57 mmol), (R)-3-(tert-butoxycarbonylamino)piperidine (3.0 g, 12.67 mmol), and K2CO3 (2.63 g, 19.01 mmol) were taken up in DMF (25 mL) in a 50 mL flask. The reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with EtOAc (100 mL), washed with water (50 mL, ×2), dried over MgSO4, filtered, and the solvent evaporated in vacuo. The residue was purified by flash chromatography (6-50% EtOAc/hexanes) to give (R)-tert-butyl 1-(2-fluoro-6-methoxybenzyl)piperidin-3-ylcarbamate. MS ESI calc'd. For C18H22FN2O3 [M+1]+ 339. found 339.

Workup

  1. washwashed with water (50 mL, ×2)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by flash chromatography (6-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f21a0b55b1094d4f92cbce18a0dade13
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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