(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid → HCID 24748205, compound

HRID 1435781Notes

Reaction equation

HRID 1435781 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:13]([NH:20][CH3:21])[CH2:12]1.C1(C)C=CC(C([C@](C(O)=O)(O)[C@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@@H:13]([NH:20][CH3:21])[CH2:12]1

Participants

3

Reactant 2

HCID 22860073(2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acidHCID 24886833HCID 24886833, compound

Product 1

HCID 24748205HCID 24748205, compound

Conditions

Temperature
50 °C

Procedure

To a solution of the racemate cis-3-(7-Fluoro-1H-indol-3-yl)-indan-1-yl-methyl-amine (409 mg/2ml EtOH) was added a solution of Di-p-toluoyl-D-tartaric acid (1 eq; 564 mg/2 ml Acetone). The mixture was heated to 50° C. and stirred for 15min. Evaporated the solvent and triturated with acetone (2 ml). The white solid (84% ee) was collected and stirred with 10 ml hot EtOH for 30 min. The remaining white solid was collected and converted to free base to give [(1S,3R)-3-(7-Fluoro-1H-indol-3-yl)-indan-1-yl]-methyl-amine (93% ee).

Workup

  1. customEvaporated the solvent
  2. customtriturated with acetone (2 ml)
  3. customThe white solid (84% ee) was collected
  4. stirringstirred with 10 ml hot EtOH for 30 min
  5. customThe remaining white solid was collected

Sources & evidence

ORD record
ord-b774379326b44fbc8c0f6754dc62b6be
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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