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

HRID 715107노트

반응식

HRID 715107 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 5229333,3-Dimethylcyclobutane-1-carboxamide수율 89%

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-096c5b4a17544a54b36bfe2ecec60c0f
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187474B2

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