Acetamide → trans-1-Acetamido-2-indanol

HRID 1449840Notes

Reaction equation

HRID 1449840 reaction equation
N[C@@H:2]1CCC[C@H:3]1[OH:7].[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].[CH2:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:21]([NH2:28])[C@@H:20]1[OH:29].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(N)(=O)C>>[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.[C:3]([NH:28][C@@H:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:19][C@H:20]1[OH:29])(=[O:7])[CH3:2]

Participants

8

Reactant 6

HCID 178AcetamideHCID 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 2

HCID 15760043trans-1-Acetamido-2-indanolHCID 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)-1-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)-1-amino-2-indanol. When the amino alkanol is partially resolved trans-1-amino-2-indanol and the amide is a benzamide or acetamide, an additional step of recrystallizing the benzamide or acetamide produces substantially optically pure trans-1-benzamido-2-indanol or trans-1-acetamido-2-indanol.

Workup

  1. customan additional step of recrystallizing the benzamide or acetamide

Sources & evidence

ORD record
ord-066ec8aa9d164012a1cd1fe90b24d126
Source dataset
uspto-grants-1997_02
Patent number
US05599985

Reaction notes

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