(1R,2S)-(+)-cis-1-Amino-2-indanol → Indene

HRID 52819

Reaktionsgleichung

Reaktionsgleichung von HRID 52819
N[C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1O.N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O>>[CH2:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Komponenten

3

Edukt 2

HCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Produkt 1

HCID 7219Indene

Versuchsvorschrift

The trans amide can be made from the epoxide either (1) by treating the indene oxide with ammonia or a primary amine to produce a trans-1-amino-2-indanol and reacting the trans-1-amino-2-indanol with an acylating agent, or (2) by treating the epoxide with an amide anion to produce the trans hydroxy amide directly. In one embodiment the indene is oxidized with aqueous hypochlorite in the presence of a chiral salen catalyst to produce a partially resolved epoxide, which is converted to the partially resolved trans-1-amino-2-indanol by treating with ammonia or a primary amine followed by acylating with benzoyl chloride or acetic anhydride. The resulting benzamide or acetamide is recrystallized to yield substantially optically pure trans-1-benzamido-2-indanol or trans-1-acetamido-2-indanol. In two preferred embodiments, the cis-1-amino-2-indanols are (1S,2R)-1-amino-2-indanol and (1R,2S)-1-amino-2-indanol, produced by oxidation of indene in the presence of an R,R or S,S-salen catalyst respectively.

Quellen und Nachweise

ORD-Eintrag
ord-03ac5c50e00d4380b377431b60ad5e1f
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616808

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