L-Tartaric acid → HCID 69946670, compound

HRID 1356610Notes

Reaction equation

HRID 1356610 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.CN(C=O)C>[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

5

Reactant 2

HCID 444305L-Tartaric acidHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 69946670HCID 69946670, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

Racemic cis-1-amino-2-indanol (66.6 g, water wet, content 81.1%) was dissolved in 180 ml of methanol with 10 ml of DMF at reflux. Then 65 g of (R,R)-tartaric acid dissolved in 200 ml of methanol were added. Stirring of the mixture was continued for one hour at reflux and then it was cooled down again to 20° C. and isolation by filtration was effected. The solid was washed twice with 120 ml of methanol. After drying, 54.8 g of (1S,2R)-1-amino-2-indanol-(R,R)-tartrate methanol solvate were obtained with an e.e. of 97.0%.

Workup

  1. temperatureat reflux
  2. additionwere added
  3. temperatureat reflux
  4. filtrationisolation by filtration
  5. washThe solid was washed twice with 120 ml of methanol
  6. customAfter drying

Sources & evidence

ORD record
ord-63d1c8f887ba40ce9914499fecb20ada
Source dataset
uspto-grants-2003_07
Patent number
US06586634B1

Reaction notes

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