Ethanol → HCID 57516500, compound

HRID 1841960Notes

Reaction equation

HRID 1841960 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[Cl-].[NH4+]>[Fe].O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 67194531HCID 67194531, compound

Product 1

HCID 57516500HCID 57516500, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

4-(4-Nitro-benzenesulfonyl)-piperidine-1-carboxylic acid tert-butyl ester (0.15 g, 0.4 mmol) was suspended in a 5:1 mixture of ethanol and water (3 ml). To this solution was added iron powder (0.4 g, 0.98 mmol) followed by saturated ammonium chloride solution (1 ml) and the mixture was stirred at room temperature for 18 hours. After this time, the reaction mixture was filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.114 g, 83% yield) as a yellow solid. Tr=1.37 min, m/z (ES+) (M+Na)+ 363.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of celite
  2. washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
  3. concentrationthe solution was concentrated under vacuum
  4. customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
  5. customthe organic layer was separated
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e06ef9c322524da88e925c909c223c5f
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

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