Methylamine → HCID 59382860, compound

HRID 1254208Notes

Reaction equation

HRID 1254208 reaction equation
CS(O[CH2:6][C@@H:7]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:8][CH:9]1[CH2:14][CH2:13][C:12]([F:16])([F:15])[CH2:11][CH2:10]1)(=O)=O.[CH3:25][NH2:26]>CCOC(C)=O>[F:15][C:12]1([F:16])[CH2:13][CH2:14][CH:9]([CH2:8][C@H:7]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:6][NH:26][CH3:25])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59383018HCID 59383018, compound

Product 1

HCID 59382860HCID 59382860, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

(S)-2-(tert-butoxycarbonylamino)-3-(4,4-difluorocyclohexyl)propyl methanesulfonate (28.8 g, 0.077 mol) was dissolved in alcoholic of methylamine solution (350 mL) and the reaction was warmed at 50-60° C. overnight. The reaction mixture was cooled to rt and the solvent was removed under reduced pressure to give an oil, which was dissolved into EtOAc, washed with water twice and brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography to afford (S)-tert-butyl 1-(4,4-difluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate (8.1 g, 34.4%). 1H NMR (400 MHz, CDCl3): 5.12 (m, 1H), 4.97 (m, 1H), 3.82 (m, 1H), 3.63 (dd, J=14.4&4.4 Hz, 1H), 3.45 (dd, J=14.4&9.2 Hz, 1H), 2.76&2.74 (s, 1H), 2.20-1.20 (m, 11H), 1.44 (s, 9H); MS (E/Z): 307 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customthe solvent was removed under reduced pressure
  3. customto give an oil, which
  4. washwashed with water twice
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-93671f4dc2ea47d3b6207c0b5cb7fc32
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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