N-bromobutanimide → HCID 58551010, compound

HRID 1908072Notes

Reaction equation

[CH:1]1[N:9]2[C:4]([C:5]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[O:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)=[CH:3][CH:2]=1.C1C(=O)N([Br:33])C(=O)C1>C(Cl)Cl.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:33][C:1]1[N:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]3([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[C:4]2=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To tert-butyl spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (13.2 g, 38.8 mmol) in CH2Cl2 (125 mL) at 0° C. was added NBS (7.25 g, 40.7 mmol) in CH2Cl2 (25 mL) dropwise over 10 min. The mixture was stirred at 0° C. for 5 min before it was diluted with 200 mL of 0.5M Na2S2O3. The aqueous phase was removed and the organic phase was washed with 200 mL of brine. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (0-30% EtOAc/hexanes) to give tert-butyl 1-bromospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-carboxylate. ESI-MS m/z calc. 418.1. found 419.0 (M+1)+; Retention time: 2.29 minutes (3 min run).

Workup

customThe aqueous phase was removed
washthe organic phase was washed with 200 mL of brine
customThe organic phase was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-217b49d0ba914aa1b2d87ab0e8532e4b
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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