Sodium Hydroxide → tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

HRID 2423200Notes

Reaction equation

[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[N:12](S(C1C=CC=CC=1)(=O)=O)[CH:11]=[CH:10]3.[OH-].[Na+]>CCO>[CH3:1][CH:2]1[C:8]2=[C:9]3[C:13](=[CH:14][CH:15]=[C:7]2[O:6][CH2:5][CH2:4][N:3]1[C:25]([O:27][C:28]([CH3:29])([CH3:31])[CH3:30])=[O:26])[NH:12][CH:11]=[CH:10]3

Participants

Conditions

Temperature: 70 °C

Procedure

To tert-butyl 1-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 41, 1.5 g, 3.4 mmol) dissolved in EtOH (50 mL), 2 M NaOH (10 mL, 20 mmol) was added and the reaction mixture was heated at 70° C. for 2 hours. The EtOH was removed under reduced pressure and the water phase was extracted with DCM (2×100 mL). The organic layer was collected, dried (MgSO4) and evaporated to afford the title compound (0.98 g) as a yellow solid. MS m/z 303 [M+H]+.

Workup

customThe EtOH was removed under reduced pressure
extractionthe water phase was extracted with DCM (2×100 mL)
customThe organic layer was collected
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-25eb8c9d111e4340b0b1cd7b44871194
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

Loading…