Sodium cyanoborohydride → 1-Isopropyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

HRID 2423195Notes

Reaction equation

[CH:1]([C:4]1[C:10]2=[C:11]3[C:15](=[CH:16][CH:17]=[C:9]2[O:8][CH2:7][CH2:6][N:5]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]3)([CH3:3])[CH3:2].[BH3-]C#N.[Na+]>CCO>[CH:1]([CH:4]1[C:10]2=[C:11]3[C:15](=[CH:16][CH:17]=[C:9]2[O:8][CH2:7][CH2:6][NH:5]1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[CH:12]3)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To 1-isopropyl-8-(phenylsulfonyl)-3,8-dihydro-4H-[1,4]oxazepino[6,7-e]indole (Intermediate 38, 120 mg, 0.330 mmol) dissolved in EtOH (5 mL), NaCNBH3 (41 mg, 0.65 mmol) was added and the reaction mixture was heated at 70° C. for 30 minutes. The reaction was quenched by addition of water and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (35 mg). MS m/z 371 [M+H]+.

Workup

customThe reaction was quenched by addition of water
customthe solvent was removed under reduced pressure
customThe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record: ord-7ccf21a9414f4132bd4404d08192f886
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960374B2

Reaction notes

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