Sodium hydride → tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

HRID 1468824Notes

Reaction equation

HRID 1468824 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31]I)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([C@H:28]2[CH2:30][C@H:29]2[CH2:31][O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3801026(4-Methanesulfonylphenyl)methanolHCID 86717780tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

Product 1

HCID 86717779tert-butyl-4-[(1R,2R)-2-({[4-(methylsulfonyl)benzyl]oxy}methyl)cyclopropyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-(Methylsulfonyl)benzyl alcohol (1.0 g, 5.4 mmol) was dissolved in DMF (12 mL), and sodium hydride (60 wt % dispersion in oil, 320 mg, 8 mmol) was added. The iodide from step A (2.35 g, 6.4 mmol) in DMF (12 mL) was added and the resulting solution was stirred at RT for 15 h. The solution was quenched with sat. NH4Cl, and EtOAc. The organic layer was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which provided the title compound.

Workup

  1. customThe solution was quenched with sat. NH4Cl, and EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel column chromatography (2/1 hexanes/EtOAc) which

Sources & evidence

ORD record
ord-8939a06517de45dd9a4270bc99e806fb
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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