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

HRID 2423196Notes

Reaction equation

HRID 2423196 reaction equation
[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].C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[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][N:5]1[CH3:29])[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

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 250547541-Isopropyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole

Product 1

HCID 250547551-Isopropyl-2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleYield 5.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Isopropyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 93, 25 mg, 0.068 mmol) was dissolved in methanol (4 mL) and formaldehyde (37 wt. % in H2O, 0.090 mL, 1.1 mmol) was added followed by sodium triacetoxyborohydride (72 mg, 0.34 mmol). The reaction mixture was allowed to stir at room temperature overnight, evaporated and the crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (1.4 mg). MS m/z 385 [M+H]+.

Workup

  1. customevaporated
  2. customthe crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record
ord-db8e0ef269fb4ce5b6099628e407d6bb
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

Loading…