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

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+).

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

ORD-Eintrag

ord-096c5b4a17544a54b36bfe2ecec60c0f

Quelldatensatz

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09187474B2