Methyl cyclopropanecarboxylate → Cyclopropyl[2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indol-9-yl]methanol

HRID 2423122Notes

Reaction equation

HRID 2423122 reaction equation
[CH3:1][N:2]1[CH2:24][C:7]2=[C:8]3[C:12](=[CH:13][CH:14]=[C:6]2[O:5][CH2:4][CH2:3]1)[N:11]([S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH:10]=[CH:9]3.[Li]CCCC.[CH:30]1([C:33](OC)=[O:34])[CH2:32][CH2:31]1>C1COCC1>[CH:30]1([CH:33]([C:10]2[N:11]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[C:12]3[C:8]([CH:9]=2)=[C:7]2[CH2:24][N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]2=[CH:14][CH:13]=3)[OH:34])[CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 76122Methyl cyclopropanecarboxylateHCID 250557762-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indoleHCID 178418339Butyllithium

Product 1

HCID 25057076Cyclopropyl[2-methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indol-9-yl]methanolYield 4.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole (Example 5, 0.030 g, 0.088 mmol) was dissolved in dry THF (1 mL) at −78° C. under an atmosphere of nitrogen gas. BuLi (2.5 M in hexanes, 0.053 mL, 0.13 mmol) was added. The solution was stirred for 15 minutes before methyl cyclopropane carboxylate (0.013 mL, 0.13 mmol) was added. The temperature of the reaction mixture was allowed to rise to room temperature overnight. The crude product was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (1.5 mg). MS m/z 413 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-2141ee572c104611a635b5f22deb59fe
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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