Sodium borohydride → (7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]-oxazine-4,4'-piperidine]-1'-yl)(4-(2-hydroxyethyl)-3-methoxyphenyl)methanone

Participants

Reaction Steps

To 2-(4-(7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbon-yl)-2-methoxyphenyl)acetaldehyde (from Step 1) was added MeOH (1 mL) followed by NaBH4 (95 mg, 2.5 mmol) and the reaction was stirred for 30 minutes at ambient temperature. After 30 minutes, the mixture was filtered and the filtrate was purified by prep-HPLC (1-99% MeOH:H2O) to give (7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]-oxazine-4,4′-piperidine]-1′-yl)(4-(2-hydroxyethyl)-3-methoxyphenyl)methanone (16 mg, 7%). ESI-MS m/z calc. 452.2. found 453.2 (M+1)+. Retention time: 2.91 minutes (4.5 min run). (7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(3-fluoro-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)methanone [ESI-MS m/z calc. 468.2. found 469.4 (M+1)+. Retention time: 3.06 minutes (4.5 min run)] and (7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-(1-hydroxy-2-methylpropan-2-yl)phenyl)methanone [ESI-MS m/z calc. 450.2. found 451.2 (M+1)+. Retention time: 9.72 minutes (15 min run)] were prepared using the procedures described above.

Provenance & Evidence