Trifluoroacetic acid → HCID 59533562, compound

HRID 1873710Notes

Reaction equation

HRID 1873710 reaction equation
[CH2:1]([N:8]1[CH2:13][C@H:12]([CH2:14][Cl:15])[C@H:11]2[O:16][C@@](OC)(C)[C@](OC)(C)[O:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([N:8]1[CH2:13][C@H:12]([CH2:14][Cl:15])[C@@H:11]([OH:16])[C@H:10]([OH:19])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59533567HCID 59533567, compound

Product 1

HCID 59533562HCID 59533562, compound

Procedure

To a solution of (2S,3S,4aR,8S,8aR)-6-benzyl-8-(chloromethyl)-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridine (2) (2.2 g, 5.9 mmol) in dicholoromethane (15 mL) was added trifluoroacetic acid (0.35 mol, 26 mL). Reaction mixture was heated at reflux for about 1 hour at which point reaction was judged complete by TLC. Excess solvent and TFA were evaporated in vacuo and the residue was chromatographed using silica gel (2-8% MeOH in CHCl3). Fractions were combined and evaporated to give (1.3 g, 87%) as the title compound. Product was characterized via HPLC/MS (MH+=255) and judged to be >95% pure.

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for about 1 hour at which point reaction
  4. customExcess solvent and TFA were evaporated in vacuo
  5. customthe residue was chromatographed
  6. customevaporated

Sources & evidence

ORD record
ord-c25df8c4220f4e4196d5992cb599a1a7
Source dataset
uspto-grants-2012_11
Patent number
US08304429B2

Reaction notes

Loading…