Methanol → HCID 58017425, compound

HRID 451987Notes

Reaction equation

HRID 451987 reaction equation
[C:1]([CH2:3][O:4][C@@H:5]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)#[N:2].S(C)C.CO>C1COCC1>[NH2:2][CH2:1][CH2:3][O:4][C@@H:5]([C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 67364717HCID 67364717, compound

Product 1

HCID 58017425HCID 58017425, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-tert-Butyl 3-((R)-(cyanomethoxy)(m-tolyl)methyl)piperidine-1-carboxylate (20 g, 0.04 mol) was dissolved in anhydrous THF (300 mL), and the solution was heated to reflux under nitrogen. A solution of BH3.Me2S (12 mL, 0.12 mol) in THF was added dropwise, and stirring was continued under reflux overnight. The resulting solution was cooled to rt and MeOH was added dropwise to quench the excess borane. After evaporation of the solution, the crude (R)-tert-butyl 3-((R)-(2-aminoethoxy)(m-tolyl)methyl)piperidine-1-carboxylate was obtained and used without further purification.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under nitrogen
  3. temperatureunder reflux overnight
  4. customto quench the excess borane
  5. customAfter evaporation of the solution

Sources & evidence

ORD record
ord-9ab529715e424051bd5abe338a5d780b
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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