Trifluoroacetic acid → (R)-2-phenyl-2-(piperidin-1-yl)acetic acid

Reaction equation

[C:1]1([C@@H:7]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([O:10]C(C)(C)C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[C:1]1([C@@H:7]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59166413Tert-butyl (R)-2-phenyl-2-(piperidin-1-YL)acetate

Product 1

HCID 1090523(R)-2-phenyl-2-(piperidin-1-yl)acetic acid

Procedure

The product from Example 92A was treated with TFA (1.5 mL) at rt for 3 h. The volatiles were removed under vacuum, the residue concentrated from toluene (×2) and dried in a vacuum oven to give title compound which was used without further purification. MS (DCI; M+H) m/z=220.

Workup

customThe volatiles were removed under vacuum
concentrationthe residue concentrated from toluene (×2)
customdried in a vacuum oven

Sources & evidence

ORD record: ord-a5b2d71ed6074ce386e3a9f264b4284b
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

Loading…