Sodium hydride → (S)-tert-butyl 3-((2-nitro-4-sulfamoylphenoxy)methyl)pyrrolidine-1-carboxylate

HRID 2168030Notes

Reaction equation

HRID 2168030 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29]>O1CCCC1>[N+:28]([C:19]1[CH:20]=[C:21]([S:24](=[O:26])(=[O:25])[NH2:27])[CH:22]=[CH:23][C:18]=1[O:1][CH2:2][C@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1514341tert-butyl (3S)-3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 67126840(S)-tert-butyl 3-((2-nitro-4-sulfamoylphenoxy)methyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (0.300 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.238 g). After stirring for 15 minutes, 4-fluoro-3-nitrobenzenesulfonamide (0.295 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 (5.96 mL). The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 12 g) eluting with a gradient of 0.2% to 2% methanol/dichloromethane over 30 minutes (flow=36 m/minute) gave the title compound.

Workup

  1. customreaction
  2. stirringstirred at room temperature
  3. waitAfter 1 hour
  4. customthe reaction was partitioned between water (25 mL) and dichloromethane (50 mL)
  5. customthe reaction quenched with 1N aqueous HCl (5.96 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography (Reveleris 12 g) eluting with a gradient of 0.2% to 2% methanol/dichloromethane over 30 minutes (flow=36 m/minute)

Sources & evidence

ORD record
ord-b6da0084777647b69955f455a424beb1
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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