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

HRID 1499517ノート

反応式

HRID 1499517 の反応式
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][N:11]=[C:10]3[CH2:17][CH2:18][CH2:19][C:9]=23)[CH2:5][C@@H:4]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3]1.C1C=C(Cl)C=C(C(OO)=[O:36])C=1.[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][N+:11]([O-:36])=[C:10]3[CH2:17][CH2:18][CH2:19][C:9]=23)[CH2:5][C@@H:4]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:3]1

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 86726747tert-Butyl [(3S,5R)-5-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

生成物 1

HCID 90296528tert-Butyl [(3S,5R)-5-methyl-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate収率 59.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl [(3S,5R)-5-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (32.3 mg, 0.086 mmol) in DCM (0.50 mL) at 0° C. was added mCPBA (25.0 mg, 0.112 mmol). The reaction mixture was stirred at room temperature for 1 h. The mixture was treated with Na2S2O3 solution, followed by 1N NaOH, and stirred for 30 min. at room temperature. The organic layer was separated, dried, filtered and concentrated under vacuum to give the crude N-oxide product. The crude product was purified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to afford the sub-title compound (20 mg, 40%). LCMS calc. for C19H29N4O5 (M+H)+: m/z=393.2. Found: 393.1.

後処理

  1. stirringstirred for 30 min. at room temperature
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude N-oxide product
  7. customThe crude product was purified by preparative LC-MS (XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min.
  8. washeluting with a gradient of MeCN and water with 0.1% NH4OH)

出典と根拠

ORDレコード
ord-4821b88a7337470dba72c1847bb351f4
出典データセット
uspto-grants-2015_12
特許番号
US09200004B2

反応ノート

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