3-(Trifluoromethyl)benzaldehyde → HCID 56604362, compound

HRID 1667103Notes

Reaction equation

HRID 1667103 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(O)(=O)C>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 679903-(Trifluoromethyl)benzaldehydeHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 56604362HCID 56604362, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent2×

Procedure

To a solution of tert-butyl piperidin-4-ylcarbamate (0.15 g, 0.75 mmol) and 3-(trifluoromethyl)benzaldehyde (0.12 mL, 0.156 mmol) in dichloroethane (5 mL) was added sodium triacetoxyborohydride (0.24 g, 1.12 mmol) and a few drops of acetic acid, and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with dichloroethane and washed with saturated aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, and chromatographed on silica gel, eluting with 30% ethyl acetate/hexane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.45 (m, 3H), 4.41 (m, 1H), 3.50 (m, 2H), 3.50 (m, 1H), 2.77 (d, J=12.21 Hz, 2H), 2.11 (t, J=11.70 Hz, 2H), 1.91 (d, J=11.53 Hz, 2H), 1.41 (s, 9H), 1.34 (m, 2H); MS (DCI) m/z 359 (M+H)+.

Workup

  1. washwashed with saturated aqueous NaHCO3 solution
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customchromatographed on silica gel
  5. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e27c6e5bea9c4c29953617b1f0abb177
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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