Methylamine → (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate

HRID 451760Notes

Reaction equation

HRID 451760 reaction equation
CS(O[CH2:6][C@@H:7]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][C:9]1([F:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)=O.[CH3:24][NH2:25]>C(O)C>[F:15][C:9]1([CH2:8][C@H:7]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:6][NH:25][CH3:24])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86639447(S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate

Product 1

HCID 68710746(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Crude (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate and (n-Bu)4N+T (249 mg, 1.0 mmol) were dissolved in 33% methylamine in ethanol (50 mL). The mixture was heated to 50° C. for 17 h. The solution was cooled to rt and the volatile materials were removed in vacuo. The residue was dissolved in ether, washed with brine, dried over Na2SO4, filtered and evaporated. To afford crude (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate.

Workup

  1. temperatureThe solution was cooled to rt
  2. customthe volatile materials were removed in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-995d78ba016744d28f3160f21a1834c1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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