Benzamide → trans-1-Benzamido-2-indanol

HRID 440175Notes

Reaction equation

HRID 440175 reaction equation
N[C@@H]1CCC[C@H]1O.[NH2:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[OH:18].C1C2C(=CC=CC=2)[C@H](N)[C@@H]1O.C1C2C(=CC=CC=2)[C@@H](N)[C@H]1O.[C:41](N)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[C:41]([NH:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[OH:18])(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 5

HCID 2331BenzamideHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 69311541-Amino-2-indanol, trans-(-)-2×HCID 9866743(1S,2R)-(-)-1-Amino-2-indanolHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol3×

Product 1

HCID 54228512trans-1-Benzamido-2-indanol

Procedure

In one embodiment the trans-1-amino-2-hydroxycyclopentane may be trans-1-amino-2-indanol. If the trans-1-amino-2-hydroxycyclopentane is trans-(1S,2S)-amino-2-indanol, it is converted to cis-(1S, 2R)-1-amino-2-indanol; if the trans-1-amino-2-hydroxycyclopentane is trans-(1R,2R)-1-amino-2-indanol, it is converted to cis-(1R,2S)-l-amino-2-indanol. When the amino alkanol is partially resolved trans-1-amino-2-indanol and the amide is a benzamide, an additional step of recrystallizing the benzamide produces substantially optically pure trans-1-benzamido-2-indanol.

Workup

  1. customan additional step of recrystallizing the benzamide

Sources & evidence

ORD record
ord-316e17a4eed543f8b127d5fac5098b11
Source dataset
uspto-grants-1996_05
Patent number
US05516943

Reaction notes

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