D-Tartaric acid → HCID 118123600, compound

HRID 2040397Notes

Reaction equation

HRID 2040397 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:12])[CH2:3]1.[C:14]([OH:23])(=[O:22])[C@H:15]([C@@H:17]([C:19]([OH:21])=[O:20])[OH:18])[OH:16]>CO>[C:14]([OH:23])(=[O:22])[C@H:15]([C@@H:17]([C:19]([OH:21])=[O:20])[OH:18])[OH:16].[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[CH:4]([CH3:12])[CH2:3]1

Participants

4

Reactant 2

HCID 439655D-Tartaric acidHCID 112175411,1,3-Trimethylindan-4-amine

Product 1

HCID 118123600HCID 118123600, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Three hundred grams (300 g) of racemic 1,1,3-trimethyl-4-aminoindane, 128 g of D-tartaric acid and 260 ml of methanol were mixed, and the mixture was kept at 70° C. for 1 hour. Then, the mixture was left to cool to room temperature, and about 0.1 g of a seed crystal was mixed and the mixture was allowed to stand for 2 days. The generated solid was filtrated off, and washed with methanol. The resultant solid was re-crystallized from methanol five times to obtain 100 g of 1,1,3-trimethyl-4-aminoindane D-tartarate. To 78 g of the resultant 1,1,3-trimethyl-4-aminoindane D-tartarate was added a 5% sodium hydroxide aqueous solution until pH reached 10 or more, and the mixture was extracted with methyl t-butyl ether three times. The resultant oil layers were washed with saturated saline and a saturated sodium hydrogen carbonate aqueous solution sequentially, then, dried over sodium sulfate and concentrated under reduced pressure to obtain 38 g of a mixture of 1,1,3-trimethyl-4-aminoindane in which the enantiomer ratio (R form/S form) was 99.6/0.4.

Workup

  1. waitThen, the mixture was left
  2. additionabout 0.1 g of a seed crystal was mixed
  3. waitto stand for 2 days
  4. filtrationThe generated solid was filtrated off
  5. washwashed with methanol
  6. customThe resultant solid was re-crystallized from methanol five times

Sources & evidence

ORD record
ord-bf441c12088441e5be3002e6cd00aa0d
Source dataset
uspto-grants-2013_11
Patent number
US08580836B2

Reaction notes

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