Sodium Hydroxide → tert-Butyl [(3S)-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

HRID 924403Notes

Reaction equation

HRID 924403 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[N+:12]([C:15]1[C:16]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]2)=[C:17]2[CH2:23][CH2:22][CH2:21][C:18]2=[N:19][CH:20]=1)([O-:14])=[O:13].[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[N+:12]([C:15]1[C:16]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:36])[CH3:35])[CH2:25]2)=[C:17]2[CH2:23][CH2:22][CH2:21][C:18]2=[N+:19]([O-:9])[CH:20]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86726687tert-Butyl [(3S)-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

Product 1

HCID 86726692tert-Butyl [(3S)-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamateYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (198 mg, 0.883 mmol) was slowly added to a solution of tert-butyl [(3S)-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (301.0 mg, 0.8305 mmol) in DCM (1.06 mL) at 0° C. The reaction mixture was stirred at room temperature for 67 h. The mixture was treated with aq, Na2S2O3 and 1 M NaOH, and then stirred for 30 min. at room temperature. The reaction mixture was extracted three times with DCM. The combined organic extract was dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (277 mg, 88%) as light orange powder. LCMS calc. for C18H27N4O5 (M+H)+: m/z=379.3. Found: 379.2.

Workup

  1. stirringstirred for 30 min. at room temperature
  2. extractionThe reaction mixture was extracted three times with DCM
  3. extractionThe combined organic extract
  4. dry with materialwas dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18ea929ca3bd488199d7dad95cd9ffc1
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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