Trifluoroacetic acid → HCID 118006597, compound

HRID 1486805Notes

Reaction equation

HRID 1486805 reaction equation
[OH:1][C@@H:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[C@@H:3]1[O:8][C@H:7]([CH3:9])[CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:9][C@@H:7]1[CH2:6][NH:5][CH2:4][C@H:3]([C@H:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[OH:1])[O:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118007368HCID 118007368, compound

Product 1

HCID 118006597HCID 118006597, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (2R,6R)-tert-butyl 2-((S)-hydroxy(pyridin-2-yl)methyl)-6-methylmorpholine-4-carboxylate (150 mg, 0.486 mmol) in DCM (5 mL) was added TFA (1 mL) followed by stifling at rt for 1 h. The completed reaction was concentrated and azeotroped to dry three times with toluene (5 mL each) followed by diluting with DCM (10 ml) washing two times with saturated NaHCO3 in water (2 mL), brine (2 mL), drying over MgSO4, filtering and concentration and drying in vacuo to provide crude (S)-((2R,6R)-6-methylmorpholin-2-yl)(pyridin-2-yl)methanol (97.8 mg, 0.469, 96.4% yield).

Workup

  1. customThe completed reaction
  2. concentrationwas concentrated
  3. customazeotroped
  4. dry with materialto dry three times with toluene (5 mL each)
  5. additionby diluting with DCM (10 ml)
  6. washwashing two times with saturated NaHCO3 in water (2 mL), brine (2 mL)
  7. dry with materialdrying over MgSO4
  8. filtrationfiltering
  9. concentrationconcentration
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-6a857f18d7d44e4e85aec97ffd0bc168
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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