m-Chloroperbenzoic acid → tert-Butyl [(3R,4R,5S)-4-hydroxy-5-methyl-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

HRID 1499493Notes

Reaction equation

HRID 1499493 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[OH:12][C@@H:13]1[C@@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]3[CH2:29][CH2:30][CH2:31][C:21]=23)[CH2:15][C@H:14]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]>C(Cl)Cl>[OH:12][C@@H:13]1[C@@H:18]([CH3:19])[CH2:17][N:16]([C:20]2[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N+:23]([O-:9])=[C:22]3[CH2:29][CH2:30][CH2:31][C:21]=23)[CH2:15][C@H:14]1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86726722tert-Butyl [(3R,4R,5S)-4-hydroxy-5-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

Product 1

HCID 86726723tert-Butyl [(3R,4R,5S)-4-hydroxy-5-methyl-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamateYield 43.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (0.420 g, 1.87 mmol) was slowly added to a solution of tert-butyl [(3R,4R,5S)-4-hydroxy-5-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (0.200 g, 0.510 mmol) in DCM (3.0 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 h. The mixture was then washed with aq. Na2S2O3, followed by 1 M NaOH. The organic layer was separated, dried and concentrated under reduced pressure. The resulting residue was further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc) to give the sub-title compound (90 mg, 43%) as a light orange powder. LCMS calc. for C19H29N4O6 (M+H)+: m/z=409.2. Found: 409.2.

Workup

  1. washThe mixture was then washed with aq. Na2S2O3
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was further purified by silica gel column chromatography (eluting with 0-30% MeOH in EtOAc)

Sources & evidence

ORD record
ord-3c5911e462354345834087accb9b4453
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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