Trifluoroacetic acid → HCID 58551369, compound

Temperature

25 °C

To a solution of tert-butyl 1′-methylsulfonylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (200 mg, 0.48 mmol) in dry dichloromethane (1 mL) at 0° C. was added TFA (147 μL, 1.91 mmol). The cooling bath was removed and the mixture was stirred for 1.5 h at 25° C. The mixture was concentrated under reduced pressure and the residue obtained was taken up in dichloromethane (10 ml) and was washed with aqueous saturated NaHCO3 (5 ml). The aqueous phase was extracted twice with dichloromethane (2×10 ml) and the organic phases were combined, dried, filtered and concentrated to yield 1′-methylsulfonylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine] as a light yellow foamy solid (150 mg, 99%). ESI-MS m/z calc. 318.1. found 319.3 (M+1)+; Retention time 0.93 minutes (3 min run). 1-(Methylsulfinyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine] was also prepared using the procedure described above where only one aliquot of H2O2 was used in Step 1.

1. customThe cooling bath was removed
2. concentrationThe mixture was concentrated under reduced pressure
3. customthe residue obtained
4. washwas washed with aqueous saturated NaHCO3 (5 ml)
5. extractionThe aqueous phase was extracted twice with dichloromethane (2×10 ml)
6. customdried
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-4f84ae97317642cc8fd01e3b1d9694df

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598164B2