Ammonium Hydroxide → 3,3-Dimethylcyclobutane-1-carboxamide

HRID 715107ノート

反応式

HRID 715107 の反応式
[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4]([C:6](O)=[O:7])[CH2:3]1.C(Cl)(=O)C(Cl)=O.[NH4+:16].[OH-]>C(Cl)Cl.CN(C=O)C.C1COCC1>[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4]([C:6]([NH2:16])=[O:7])[CH2:3]1

参加物

7

反応物 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 2151063,3-Dimethylcyclobutanecarboxylic acid

生成物 1

HCID 5229333,3-Dimethylcyclobutane-1-carboxamide収率 89%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Treat a solution of 3,3-dimethylcyclobutylcarboxylic acid (0.500 g, 3.90 mmol) and oxalyl chloride (0.512 mL, 5.85 mmol) in DCM (30 mL) with catalytic DMF (1 drop), stir at RT for 4 h, concentrate to dryness, add additional DCM and concentrate to dryness again. Dissolve the residue in THF (10 mL), add drop-wise to a solution of NH4OH (2 mL, 51.4 mmol) in THF (20 mL), and stir at RT overnight. Extract with EtOAc (2×), wash the combined organics with brine, dry over MgSO4 and concentrate to dryness to afford the title compound (440 mg, 89%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.07 (s, 1H); 6.63 (s, 1H); 2.86 (m, 1H); 1.85 (m, 2H); 1.74 (m, 2H); 1.10 (s, 3H); 1.00 (s, 3H); MS(ESI) m/z: 128.2 (M+H+).

後処理

  1. concentrationconcentrate to dryness
  2. additionadd additional DCM
  3. concentrationconcentrate to dryness again
  4. dissolutionDissolve the residue in THF (10 mL)
  5. additionadd
  6. stirringstir at RT overnight
  7. extractionExtract with EtOAc (2×)
  8. washwash the combined organics with brine
  9. dry with materialdry over MgSO4
  10. concentrationconcentrate to dryness

出典と根拠

ORDレコード
ord-096c5b4a17544a54b36bfe2ecec60c0f
出典データセット
uspto-grants-2015_11
特許番号
US09187474B2

反応ノート

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