Sodium hydride → HCID 66704009, compound

HRID 424438Notes

Reaction equation

HRID 424438 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[CH:8][CH:7]=1.[H-].[Na+].[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>O1CCCC1>[N:27]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C@@H:12]3[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)=[CH:8][CH:7]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 66703997HCID 66703997, compound

Product 1

HCID 66704009HCID 66704009, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl (2S)-2-(4-(3-bromopropyloxy)phenyl)morpholine-4-carboxylate (2.0 g, 5.0 mmol) was added to a solution of sodium hydride (60% in oil, 0.22 g, 5.50 mmol) and pyrrolidine (0.43 g, 6.05 mmol) in tetrahydrofuran (40 ml) at room temperature and the mixture was stirred at 80° C. for 5 hours. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish tert-butyl (2S)-2-(4-(3-(pyrrolidin-1-yl)propyloxy)phenyl)morpholine-4-carboxylate (1.13 g, 58%) as a colorless oil.

Workup

  1. customThe mixture was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-b089b24c641449d19e251ab70f9b1ef6
Source dataset
uspto-grants-2012_01
Patent number
US08106045B2

Reaction notes

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