Methanol → Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amine

HRID 2043929Notes

Reaction equation

HRID 2043929 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CO.O.CCOC(C)=O>C1COCC1>[CH:14]1([CH2:12][NH:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8857Ethyl AcetateHCID 4786080N-(4-(methylsulfonyl)phenyl)cyclopentanecarboxamide

Product 1

HCID 43453307Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen atmosphere a solution of cyclopentanecarboxylic acid (4-methanesulfonylphenyl)-amide (10 mmol) in THF (20 mL) was added a solution of 1M BH3 in THF (20 mL). The mixture was refluxed for 3H and cooled to RT. Addition of 10 mL of MeOH followed by reflux for 15 min. The mixture was cooled and added water (100 mL) and EtOAc (200 mL). The organic phase was isolated and washed with 1N NaOH, water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford cyclopentylmethyl-(4-methanesulfonylphenyl)-amine as a yellow solid.

Workup

  1. temperatureThe mixture was refluxed for 3H
  2. temperatureby reflux for 15 min
  3. temperatureThe mixture was cooled
  4. customThe organic phase was isolated
  5. washwashed with 1N NaOH, water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b82752d0c154ce9ae43384b1edc4792
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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