Trimethyl orthoformate → 8-Oxo-2-methoxy-3-oxa-1-azabicyclo[4.2.0]octane

Reaction equation

[O:1]=[C:2]1[N:9]2[CH:4]([CH2:5][CH2:6][O:7][C:8]2(C)C)[CH2:3]1.[OH:12][CH2:13]CC1NC(=O)C1.C(OC)(OC)OC>>[O:1]=[C:2]1[N:9]2[CH:4]([CH2:5][CH2:6][O:7][CH:8]2[O:12][CH3:13])[CH2:3]1

Participants

Reactant 3

HCID 9005Trimethyl orthoformate

HCID 12769226HCID 12769226, compound

HCID 12769229HCID 12769229, compound

Product 1

HCID 199939978-Oxo-2-methoxy-3-oxa-1-azabicyclo[4.2.0]octane

Procedure

Following the procedure described for the preparation of 8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane from 4-(2'-hydroxyethyl)-2-azetidinone and using trimethyl orthoformate instead of 2,2-dimethoxypropane one obtains 8-oxo-2-methoxy-3-oxa-1-azabicyclo[4.2.0]octane.

Sources & evidence

ORD record: ord-8105701b278e44e7936cf2804250b5d3
Source dataset: uspto-grants-1988_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04775669

Reaction notes

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