Water → HCID 69946670, compound

HRID 1356607Notes

Reaction equation

HRID 1356607 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].O>C(O)C.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

6

Reactant 3

HCID 962WaterHCID 444305L-Tartaric acidHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 69946670HCID 69946670, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Racemic cis-1-amino-2-indanol (25.1 g) was dissolved in 375 ml of ethanol. At room temperature a solution of (R,R)-tartaric acid (27.5 g) in 375 ml of methanol was added. The water content was less than 0.1 wt. % relative to methanol. Then the mixture was heated to 60° C. and then cooled down again to 20° C. The solid was recovered by filtration and washed with 100 ml of methanol. After drying, 23.7 g of (1S,2R)-1-amino-2-indanol-(R,R)-tartrate methanol solvate were obtained with an e.e. of 93.1%. D[v, 0.9]=92.7 μm (measured with a Malvern 2600 apparatus).

Workup

  1. temperaturecooled down again to 20° C
  2. filtrationThe solid was recovered by filtration
  3. washwashed with 100 ml of methanol
  4. customAfter drying

Sources & evidence

ORD record
ord-46bd610437f2468c8c6d4f658c47137a
Source dataset
uspto-grants-2003_07
Patent number
US06586634B1

Reaction notes

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