Cyclopropylamine → tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

HRID 2408837Notes

Reaction equation

HRID 2408837 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]1([NH2:18])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(O)(=O)C.ClCCl>[CH:15]1([NH:18][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 69828CyclopropylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate 90.3 g, 1.5 mmol) in dichloroethane (10 mL) was add cyclopropylamine (0.13 mL, 1.95 mmol), sodium triacetoxyborohydride (0.48 g, 2.26 mmol) and a few drops of acetic acid. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with dichloromethane and washed with NaHCO3 solution. The organic phase was separated and then dried over MgSO4. Following concentration, the residue was chromatographed on silica gel eluting with 5% methanol/dichloromethane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 4.03 (d, J=12.21 Hz, 2 H), 2.79 (m, 3 H), 2.14 (m, 1 H), 1.91 (d, J=12.55 Hz, 2 H), 1.69 (m, 2 H), 1.46 (m, 9 H), 1.27 (m, 2 H), 0.47 (m, 2 H), 0.36 (m, 2 H).

Workup

  1. washwashed with NaHCO3 solution
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentration
  5. customthe residue was chromatographed on silica gel eluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-8eaeb56113804408a9c682967adb7b72
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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