Water → methyl[1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic Acid, 1,1-dimethylethyl Ester

HRID 38286Notes

Reaction equation

HRID 38286 reaction equation
[H-].[Na+].[C:3]1([S:9]([N:12]2[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:25]I.O>O1CCCC1>[CH3:25][N:17]([CH:14]1[CH2:15][CH2:16][N:12]([S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:10])=[O:11])[CH2:13]1)[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86631068[1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic acid, 1,1-dimethylethyl Ester

Product 1

HCID 86631067methyl[1-(phenylsulfonyl)-3-pyrrolidinyl]-carbamic Acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil) (49 mg) in tetrahydrofuran (10 ml) was added the product from part (a) (400 mg) as a solution in tetrahydrofuran (5 ml). After 30 minutes methyl iodide (90 ul) was added and the reaction stirred overnight. The mixture was poured into water and the organics extracted into ether. The ether extractions were combined, washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. Purification by column chromatography (eluent 20% EtOAc/Hexane) gave the subtitle compound as an oil (235 mg).

Workup

  1. extractionthe organics extracted into ether
  2. extractionThe ether extractions
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give crude product
  7. customPurification by column chromatography (eluent 20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-9a0be007a6a04a8ea00f5bd270720b31
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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