Acetic Acid → HCID 54793808, compound

HRID 2169983Notes

Reaction equation

HRID 2169983 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.ClCCCl.C(Cl)Cl.[OH-].[Na+]>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 312444-MethoxybenzaldehydeHCID 4207714-PiperidinemethanolHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 54793808HCID 54793808, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolventHCID 21493386Dce thfSolvent

Procedure

To a solution of 4-piperidinemethanol (2.28 g, 19.78 mmol) and 4-methoxybenzaldehyde (2.30 mL, 19.77 mmol) in THF/DCE (1:1 by volume, 100 mL) was added acetic acid (1 mL), followed by NaBH(OAc)3 (16.76 g, 79.08 mmol) in small portions. The reaction mixture was stirred at room temperature overnight under N2. The reaction was diluted with DCM and basified to pH=10 with 2 N NaOH solution. The organic layer was separated, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (Eluent: 60% EtOAc in hexanes) to give the title compound as a pale yellow oil (2.13 g, 46%). 1H NR (400 MHz, DMSO-d6) δ 1.04-1.13 (m, 2H), 1.28-1.32 (m, 1H), 1.58-1.61 (m, 2H), 1.79-1.86 (m, 2H), 2.75-2.77 (m, 2H), 3.22 (t, J=8.0 Hz, 2H), 3.34 (s, 2H), 3.72 (s, 3H), 4.38 (t, J=4.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.0 Hz, 2H). MS 236 (MH+).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (Eluent: 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3b54e63e3ad74a4d99bea1e67d60ada2
Source dataset
uspto-grants-2015_06
Patent number
US09049878B2

Reaction notes

Loading…