tert-Butyl 3-oxa-7,9-diazabicyclo(3.3.1)nonane-7-carboxylate → tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate

HRID 2281301Notes

Reaction equation

[CH:1]12[NH:16][CH:5]([CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]1)[CH2:4][O:3][CH2:2]2.[CH3:17][C:18]1[C:26]2[CH2:25][O:24][C:23](=[O:27])[C:22]=2[CH:21]=[CH:20][C:19]=1[C@@H:28]1[CH2:30][O:29]1>C(O)C>[OH:29][C@H:28]([C:19]1[CH:20]=[CH:21][C:22]2[C:23](=[O:27])[O:24][CH2:25][C:26]=2[C:18]=1[CH3:17])[CH2:30][N:16]1[CH:1]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6][CH:5]1[CH2:4][O:3][CH2:2]2

Participants

Conditions

Temperature: 140 °C

Procedure

Commercially available tert-Butyl 3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate (300 mg, 1.3 mmol) and 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (INTERMEDIATE 2) (380 mg, 2.0 mmol) were dissolved in ethanol (10 ml) and heated in a microwave reactor at 140° C. for 1 hour. The reaction was concentrated and purified by MPLC on ISCO RediSep® purification column and eluted with 50%-100% ethyl acetate/hexane to provide tert-butyl 9-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate.

Workup

concentrationThe reaction was concentrated
custompurified by MPLC on ISCO RediSep® purification column
washeluted with 50%-100% ethyl acetate/hexane

Sources & evidence

ORD record: ord-206b9e1e71ef44f4a69c3762a8db4c51
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139585B2

Reaction notes

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