Methanol → HCID 58017391, compound

HRID 451992Notes

Reaction equation

HRID 451992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([O:23][CH2:24][C:25]#[N:26])[C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[CH:6][C:7]=1[F:8].S(C)C.CO>C1COCC1>[NH2:26][CH2:25][CH2:24][O:23][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[C@@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 67364383HCID 67364383, compound

Product 1

HCID 58017391HCID 58017391, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(R)-tert-Butyl 3-((R)-(3-chloro-4-fluorophenyl)(cyanomethoxy)methyl)piperidine-1-carboxylate (2.28 g, 6 mmol) was dissolved in anhydrous THF (50 mL), and the solution was heated to reflux under nitrogen. A solution of 10 M of BH3.Me2S (1.8 mL, 18 mmol) in THF was added dropwise and stirring was continued under reflux overnight. The resulting solution was cooled to 0° C., CH3OH was added dropwise to quench the reaction. Evaporation of the solvent led to crude (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-chloro-4-fluorophenyl)methyl)piperidine-1-carboxylate (2 g, yield 87%), which was used in the next step without further purification.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under nitrogen
  3. temperatureunder reflux overnight
  4. customto quench
  5. customthe reaction
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-99d6899e408f43faa40c8d14e980fdd1
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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