2,5-Diazabicyclo[4.1.0]heptane-2-carboxylic Acid DiMethylethyl Ester → HCID 131732970, compound

HRID 2173433Notes

Reaction equation

[CH:1]12[CH2:7][CH:6]1[NH:5][CH2:4][CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:15][C:16]1[C:24]2[CH2:23][O:22][C:21](=[O:25])[C:20]=2[CH:19]=[CH:18][C:17]=1[C@@H:26]1[CH2:28][O:27]1>CCO>[OH:27][C@H:26]([C:17]1[CH:18]=[CH:19][C:20]2[C:21](=[O:25])[O:22][CH2:23][C:24]=2[C:16]=1[CH3:15])[CH2:28][N:5]1[CH:6]2[CH:1]([CH2:7]2)[N:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][CH2:4]1

Participants

Conditions

Temperature: 145 °C

Procedure

In a microwave vial charged with stirring bar, tert-butyl (±)-2,5-diazabicyclo[4.1.0]heptane-2-carboxylate (341 mg, 1.72 mmol) was dissolved in EtOH (20 mL). 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (654 mg, 3.44 mmol) was added. Then mixture was sealed and put on microwave reactor. It was heated up to 145° C. and was stir at 145° C. for 60 minutes. After cooling down to room temperature, solution was transferred to a round bottom flask and was concentrated on rotavapor to give crude product, which was purified by ISCO (80 gram silica gel column, eluted by 0-10% MeOH/DCM gradient). Removing solvent gave the title compound. LC/MS: (M+1)+=389.14;

Workup

additionIn a microwave vial charged
customThen mixture was sealed
customput on microwave reactor
stirringwas stir at 145° C. for 60 minutes
temperatureAfter cooling down to room temperature
customsolution was transferred to a round bottom flask
concentrationwas concentrated on rotavapor
customto give crude product, which
customwas purified by ISCO (80 gram silica gel column, eluted by 0-10% MeOH/DCM gradient)

Sources & evidence

ORD record: ord-701b714595b740d99dfcb4e872fadfa2
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

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