Sodium hydride → HCID 62349516, compound

HRID 706939Notes

Reaction equation

HRID 706939 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.[H-].[Na+].F[C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30]>O1CCCC1>[N+:29]([C:20]1[CH:21]=[C:22]([S:25]([NH2:28])(=[O:26])=[O:27])[CH:23]=[CH:24][C:19]=1[O:1][CH2:2][CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 62349516HCID 62349516, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.300 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.223 g). After stirring for 15 minutes, 4-fluoro-3-nitrobenzenesulfonamide (0.276 g) was added and reaction stirred at room temperature. After 1 hour the reaction was partitioned between water (25 mL) and dichloromethane (50 mL) and the reaction quenched with 1N aqueous HCl (5.57 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. Treatment with HCl (4.0M in dioxane, 2 mL) and methanol (2 mL) for 1 hour, followed by concentration, trituration with dichloromethane and filtration gave the title compound.

Workup

  1. customreaction
  2. stirringstirred at room temperature
  3. customAfter 1 hour the reaction was partitioned between water (25 mL) and dichloromethane (50 mL)
  4. customthe reaction quenched with 1N aqueous HCl (5.57 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. waitTreatment with HCl (4.0M in dioxane, 2 mL) and methanol (2 mL) for 1 hour
  10. concentrationfollowed by concentration, trituration with dichloromethane and filtration

Sources & evidence

ORD record
ord-02efc06deca14643bc0602f95dff2e9a
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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