3-Amino-1-propanol → 3-(3-Hydroxypropyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Reaktionsgleichung

[CH2:1]1[CH:3]2[C:4]([O:6][C:7](=[O:8])[CH:2]12)=O.[NH2:9][CH2:10][CH2:11][CH2:12][OH:13]>>[OH:13][CH2:12][CH2:11][CH2:10][N:9]1[C:7](=[O:8])[CH:2]2[CH:3]([CH2:1]2)[C:4]1=[O:6]

Komponenten

Edukt 2

HCID 90863-Amino-1-propanol

HCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Produkt 1

HCID 612069603-(3-Hydroxypropyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneAusbeute 49 %

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

A mixture of cyclopropane-2,3-dicarboxylic acid anhydride (purchased at Acros, Ref 37012-0010, 500 mg, 1.0 eq.) and 3-amino-1-propanol (340 mL, 1.0 eq.) was heated 6 h at 180° C. The reaction mixture was purified on silica, eluting with a 98:2 to 19:1 gradient of dichloromethane/methanol, to yield 360 mg (49%) of the desired product as light yellow solid. MS (m/e): 168.1 (M−H−, 100%)

Aufarbeitung

customThe reaction mixture was purified on silica
washeluting with a 98:2 to 19:1 gradient of dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag: ord-af3b9f43c5cb46fbb6b027663f7badf1
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07388095B2

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