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

HRID 440178Notes

Reaction equation

HRID 440178 reaction equation
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

Participants

3

Reactant 2

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

Product 1

HCID 7219Indene

Procedure

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. The resulting benzamide is recrystallized to yield substantially optically pure trans-1-benzamido-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.

Sources & evidence

ORD record
ord-5a5a4aa0a92542b38fba3a2513e20cde
Source dataset
uspto-grants-1996_05
Patent number
US05516943

Reaction notes

Loading…