Acetic Acid → HCID 18542682, compound

HRID 1268194Notes

Reaction equation

HRID 1268194 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33]1OC(O)C[O:35][CH:34]1O.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:22]/[CH:23]=[CH:24]/[C:25]3[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=3)[C:28]#[N:29])[CH2:33][CH2:34][OH:35])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 186078Glycolaldehyde dimerHCID 5003444Sodium cyanoborohydrideHCID 18542676HCID 18542676, compound

Product 1

HCID 18542682HCID 18542682, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[3-[N-[4-(1-t-butoxycarbonylpiperidin-4-yloxy)phenyl]amino]-1-(E)-propenyl]benzonitrile (1000 mg) and glycolaldehyde dimer (277 mg) in dichloromethane (20 ml) were added acetic acid (0.13 ml) and sodium cyanoborohydride (72 mg) in an ice bath. The mixture was stirred at the same temperature for 5 hours and then at room temperature for 4 hours. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by chromatography on a silica gel column using hexane/ethyl acetate=4/3 as an eluant to give the desired compound (1100 mg, yield 50%) as a pale yellow oil.

Workup

  1. waitat room temperature for 4 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-3600ef0ddd374155ba714dd689fb3cbd
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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