Acetic Acid → tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate

HRID 591652Notes

Reaction equation

HRID 591652 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.[CH:15]([NH2:18])([CH3:17])[CH3:16].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:15]([NH:18][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)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20801236tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.09 mmol) in methanol (35 mL) was added isopropylamine (1.07 mL, 12.54 mmol), acetic acid (0.94 mL, 16.30 mmol) and sodium cyanoborohydride (1.0 g, 16.30 mmol). The resulting solution was stirred at room temperature for 1 hour, then quenched with water. The solution was concentrated in vacuo and redissolved in ethyl ether. The organics were extracted with 0.1 N HCl. The aqueous extracts were basified with 1 N NaOH (pH>8) and extracted with ethyl ether. The organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, to afford tert-butyl 4-(isopropylamino)piperidine-1-carboxylate (1.2 g, 41%) as a clear liquid.

Workup

  1. customquenched with water
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionredissolved in ethyl ether
  4. extractionThe organics were extracted with 0.1 N HCl
  5. extractionextracted with ethyl ether
  6. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56d616bad1aa4c429cedc30b1da826fd
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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