Acetic Acid → HCID 66649755, compound

HRID 419378Notes

Reaction equation

HRID 419378 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[C@H:19]12[CH2:25][C@H:22]([NH:23][CH2:24]1)[CH2:21][N:20]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([N:23]3[CH2:24][C@@H:19]4[CH2:25][C@H:22]3[CH2:21][N:20]4[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 259188571-(3-Methoxy-4-nitrophenyl)piperidin-4-one

Product 1

HCID 66649755HCID 66649755, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinone (Example 57, step B) (0.63 g, 2.5 mmol), 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 5.0 mmol), HOAc (0.23 g, 3.8 mmol), TEA (0.25 g, 2.5 mmol) in DCM (20 mL) is added sodium triacetoxyborohydride (0.81 g, 3.8 mmol). The mixture was stirred for 1 h then poured into saturated NaHCO3 solution (30 mL). The layers are separated and the aqueous layer washed with DCM. The organics are combined, dried (MgSO4), filtered and rotovaped. DCM and silica are added and the solvent removed by rotovap. After purification by silica gel chromatography, the title compound of step A (1.0 g, 2.4 mmol, 96%) is obtained as a yellow foam. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, J=9.3 Hz, 1H), 6.39 (dd, J=9.3, 2.0 Hz, 1H), 6.28 (d, J=2.0 Hz, 1H), 4.36-4.20 (m, 1H), 3.91 (s, 3H), 3.79-3.40 (m, 4H), 3.16-3.01 (m, 4H), 2.64-2.37 (m, 2H), 1.93-1.68 (m, 4H), 1.61-1.49 (m, 2H), 1.44 (s, 9H).

Workup

  1. customThe layers are separated
  2. washthe aqueous layer washed with DCM
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. additionDCM and silica are added
  6. customthe solvent removed by rotovap
  7. customAfter purification by silica gel chromatography

Sources & evidence

ORD record
ord-2d4600fefad14b20aa3c44a6423819a8
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…