Maleic Acid → HCID 69497880, compound

HRID 2085204Notes

Reaction equation

HRID 2085204 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[OH:11][C@@H:12]([CH2:33][N:34]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=2)[CH2:36][CH2:35]1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[O:23][CH2:22][C:21]([C:25]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=O)=[CH:20]2.[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]\[C:53]([OH:55])=[O:54]>C1COCC1.C(O)C>[C:50]([OH:57])(=[O:56])/[CH:51]=[CH:52]\[C:53]([OH:55])=[O:54].[OH:11][C@@H:12]([CH2:33][N:34]1[CH2:39][CH2:38][CH:37]([C:40]2[CH:49]=[CH:48][C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH:41]=2)[CH2:36][CH2:35]1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:24]=1[O:23][CH2:22][C:21]([CH2:25][N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1)=[CH:20]2

Participants

7

Reactant 4

HCID 444266Maleic AcidHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 60077895HCID 60077895, compound

Product 1

HCID 69497880HCID 69497880, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminum hydride (0.55 g) in THF was added aluminum chloride (0.63 g) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was made to become 4° C. and a solution of (S)-4-(8-(2-hydroxy-3-(4-(naphthalen-2-yl)piperidino)propyloxy)-2H-chromen-3-ylcarbonyl)morpholine (2.5 g) in THF (50 ml) was added dropwise. The mixture was stirred for 30 min and hydrous THF was added. The mixture was further stirred for 30 min at room temperature and the precipitated insoluble matter was filtered off through celite. The solvent was evaporated under reduced pressure to give a brown oil. This was dissolved in ethanol and maleic acid was added. The precipitated crystals were collected by filtration and dried to give the title compound (1.3 g) as pale-yellow crystals, melting point 164-166° C.

Workup

  1. customto become 4° C.
  2. stirringThe mixture was stirred for 30 min
  3. stirringThe mixture was further stirred for 30 min at room temperature
  4. filtrationthe precipitated insoluble matter was filtered off through celite
  5. customThe solvent was evaporated under reduced pressure
  6. customto give a brown oil
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-fb6c75e353664bc79963bbd7ff4e59c5
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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