Acetic Acid → HCID 90029300, compound

HRID 2200171Notes

Reaction equation

HRID 2200171 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].C(O[C:23]1(O[Si](C)(C)C)[CH2:25][CH2:24]1)C.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C>[CH:23]1([N:17]2[CH2:16][CH:15]=[C:14]([C:6]3[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[CH2:19][CH2:18]2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 66802126HCID 66802126, compound

Product 1

HCID 90029300HCID 90029300, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stir the mixture of 4-(3-nitro-5-(trifluoromethyl)phenyl)-1,2,3,6-tetrahydropyridine (150 mg, 0.55 mmol), (1-ethoxycyclopropoxy)trimethylsilane (700 mg, 2.4 mmol), sodium cyanoborohydride (200 mg, 3.3 mmol) and acetic acid (240 mg, 4.0 mmol) in ethanol (10 mL) at 60° C. overnight. Concentrate the mixture to get a residue, partition between EtOAc and water, collect the organic layer, wash with water and brine sequentially, and dry over anhydrous sodium sulfate. Concentrate under reduced pressure to give the product as a yellow solid (135 mg, 79%). MS: (M+1): 313.1.

Workup

  1. concentrationConcentrate the mixture
  2. customto get a residue
  3. custompartition between EtOAc and water
  4. customcollect the organic layer
  5. washwash with water and brine sequentially
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-637e25d8e0d84ae58627cab8465cab2b
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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