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

HRID 1035950
Notes
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Reaction equation

HRID 1035950 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-77e4e985ed174ce9af32b680b8bdb13f
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546399B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes