Tetrahydrofuran → HCID 66712233, compound

HRID 1262319Notes

Reaction equation

HRID 1262319 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2([C:19]#[N:20])[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].N1CCOCC1.O1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[OH:18][CH:15]1[CH2:14][CH2:13][C:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)([C:19]#[N:20])[CH2:17][CH2:16]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 66712571HCID 66712571, compound

Product 1

HCID 66712233HCID 66712233, compoundYield 11%

Conditions

Temperature
50 °C

Procedure

Into a 8-dram vial, 1-(3-Methoxy-4-nitro-phenyl)-4-oxo-cyclohexanecarbonitrile (0.450 g, 1.64 mmol), Morpholine (0.429 g, 4.92 mmol), Tetrahydrofuran (8.00 mL, 98.6 mmol) was added and stirred at 50° C. for 1 hour. Sodium triacetoxyborohydride (0.695 g, 3.28 mmol) was added and continued to heat at 50° C. overnight. The reaction was cooled to room temperature. The reaction was partitioned with saturated NaHCO3 and EtOAc. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant. The collected fractions afforded trans-1-(3-methoxy-4-nitrophenyl)-4-(morpholin-4-yl)cyclohexanecarbonitrile (0.38 g, 67%) and 4-Hydroxy-1-(3-methoxy-4-nitro-phenyl)-cyclohexanecarbonitrile (0.05 g, 10%).

Workup

  1. temperatureto heat at 50° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. customThe reaction was partitioned with saturated NaHCO3 and EtOAc
  4. customThe organic was separated
  5. washwashed with Brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe solid was filtered
  8. washwashed with DCM
  9. customThe solvent was removed under vacuum
  10. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc as eluant

Sources & evidence

ORD record
ord-15d4e0560f914f3e86524c3b9f8073fb
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…