L-Tartaric acid → HCID 69946670, compound

HRID 1356608Notes

Reaction equation

[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11].[C:12]([OH:21])(=[O:20])[C@@H:13]([C@H:15]([C:17]([OH:19])=[O:18])[OH:16])[OH:14]>CO>[NH2:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].[CH3:13][OH:14].[C:17]([C@@H:15]([C@H:13]([C:12]([OH:21])=[O:20])[OH:14])[OH:16])([OH:19])=[O:18]

Participants

Conditions

Temperature: 60 °C

Procedure

Racemic cis-1-amino-2-indanol (22.5 g, water wet, content 83.2%) was suspended with (R,R)-tartaric acid (65 g) in 120 ml of methanol of 60° C. After stirring for 1.5 hours at 60° C., 210 ml of methanol were added and the mixture was brought to reflux. At reflux a solution of racemic cis-1-amino-2-indanol (42.4 g, water wet, content 83.2%) in 120 ml of hot methanol was added. Stirring of the mixture was continued for half an hour at reflux and then it was cooled down again to 33° C. Methanol (10 ml) was added and after continued stirring (overnight) the solid was isolated by filtration and washed twice with 120 ml of methanol. After drying, 54.3 g of (1S,2R)-1-amino-2-indanol-(R,R)-tartrate methanol solvate were obtained with an e.e. of 97.5%. D[v, 0.9]=147.1 μm (measured with a Malvern 2600 apparatus).

Workup

temperatureto reflux
additionwas added
stirringStirring of the mixture
waitwas continued for half an hour
temperatureat reflux
temperatureit was cooled down again to 33° C
stirringafter continued stirring (overnight) the solid
customwas isolated by filtration
washwashed twice with 120 ml of methanol
customAfter drying

Sources & evidence

ORD record: ord-9711cf0132114e248124c4ee9fc92697
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586634B1

Reaction notes

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