Methyl iodide → (S)-10-(2-methoxymethyl-azetidin-1-yl)-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

HRID 528728Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:12]2=[C:13]([N:20]3[CH2:23][CH2:22][C@H:21]3[CH2:24][OH:25])[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[CH3:32]COC(C)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:27][CH2:26][C:12]2=[C:13]([N:20]3[CH2:23][CH2:22][C@H:21]3[CH2:24][O:25][CH3:32])[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To 57.9 mg (0.155 mmol) (S)-10-(2-hydroxymethyl-azetidin-1-yl)-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester in 10 mL anhydrous THF was added 29.8 mg (1.24 mmol, 60% dispersion in mineral oil) NaH and the reaction was cooled to 0° C. 0.4 mL (1.24 mmol) methyl iodide was added and the reaction was stirred at room temperature for 6 hours. 25 mL EtOAc was added and the organic layer was washed with H2O (2×20 mL), 20 mL saturated brine, and dried over MgSO4. After evaporation of the solvent the product was purified by column chromatography (silica, heptane/EtOAc 2:3).

Workup

washthe organic layer was washed with H2O (2×20 mL), 20 mL saturated brine
dry with materialdried over MgSO4
customAfter evaporation of the solvent the product
customwas purified by column chromatography (silica, heptane/EtOAc 2:3)

Sources & evidence

ORD record: ord-cb28632f49ae41bca2b1c983ced86da2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346816B2

Reaction notes

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