Trifluoroacetic acid → HCID 96780348, compound

HRID 530591Notes

Reaction equation

HRID 530591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)=[CH:4][C:3]=1[F:21].C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][C:3]=1[F:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118276753(R)-tert-butyl 2-(4-chloro-3-fluorophenyl)morpholine-4-carboxylate

Product 1

HCID 96780348HCID 96780348, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-butyl 2-(4-chloro-3-fluorophenyl)morpholine-4-carboxylate (990 mg) was dissolved in 2 mL of dichloromethane and TFA (2 mL) was added. The solution was stirred at room temperature for 2 h. Solvents were evaporated. The residue was extracted with dichloromethane and 1N NaOH solution. The organic layer was dried and concentrated. The residue was dried in vacuum to afford (R)-2-(4-chloro-3-fluorophenyl)morpholine an oil (669 mg). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.11 (br. s., 1H) 2.72 (dd, J=12.38, 10.36 Hz, 1H) 2.86-3.04 (m, 2H) 3.07 (dd, J=12.38, 2.53 Hz, 1H) 3.79 (td, J=11.37, 3.03 Hz, 1H) 4.05 (dd, J=11.49, 2.40 Hz, 1H) 4.48 (dd, J=10.36, 2.53 Hz, 1H) 7.02-7.13 (m, 1H) 7.15-7.23 (m, 1H) 7.33-7.42 (m, 1H).

Workup

  1. customSolvents were evaporated
  2. extractionThe residue was extracted with dichloromethane and 1N NaOH solution
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-4e3c66d6621d4e8384b2a57b31f7dbde
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

Loading…