Methylamine → tert-Butyl 4-(methylamino)piperidine-1-carboxylate

HRID 717892Notes

Reaction equation

HRID 717892 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][NH2:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:15][NH:16][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (0.50 g, 2.5 mmol, Aldrich) and 2.0 M methylamine in Tetrahydrofuran (10. mL, 20. mmol, Aldrich) was added sodium triacetoxyborohydride (1.3 g, 6.3 mmol). After stirring of the suspension overnight, the reaction was quenched with water and stirred for 1 hour. Brine was added and the product was extracted with two portions of DCM. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was used without further purification in Step 2. LCMS (M+H)+: 215.2.

Workup

  1. customthe reaction was quenched with water
  2. stirringstirred for 1 hour
  3. additionBrine was added
  4. extractionthe product was extracted with two portions of DCM
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was used without further purification in Step 2

Sources & evidence

ORD record
ord-b12d55384cdd43eab5f64cc9b99ad0f8
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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