Potassium Sodium Tartrate → HCID 68989883, compound

HRID 69483Notes

Reaction equation

HRID 69483 reaction equation
C[Al](C)C.[O:5]1[C:9]2([CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=3[F:21])[CH2:10]2)[O:8][CH2:7][CH2:6]1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[O:29][CH2:28][CH2:27]2.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(Cl)Cl>[O:8]1[C:9]2([CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:30](=[O:34])[C:31]4[CH:32]=[CH:33][C:24]([O:23][CH3:22])=[CH:25][C:26]=4[CH2:27][CH2:28][OH:29])=[CH:16][C:15]=3[F:21])[CH2:10]2)[O:5][CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 124011826-Methoxy-3,4-dihydro-1H-2-benzopyran-1-oneHCID 16682925TrimethylaluminumHCID 211054314-(1,4-Dioxa-7-azaspiro[4.4]non-7-yl)-3-fluorophenylamine

Product 1

HCID 68989883HCID 68989883, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 2M solution of trimethylaluminum in toluene (14.9 mL) was added dropwise at 0° C. to a solution of 4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenylamine (5.3 g) in methylene chloride (100.8 mL). The reaction mixture was stirred for 15 min at 0° C. and then for 30 min at room temperature. Then a solution of 6-methoxy-isochroman-1-one (3.8 g) in methylene chloride (40 mL) was added dropwise. The reaction mixture was stirred overnight at room temperature. Then saturated Rochelle salt solution was carefully added and the mixture was stirred for 1 h at room temperature. The aqueous phase was extracted several times with methylene chloride. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 416.17 (C22H25FN2O5); MS (ESI): 417 (M+H+).

Workup

  1. waitfor 30 min at room temperature
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. stirringthe mixture was stirred for 1 h at room temperature
  4. extractionThe aqueous phase was extracted several times with methylene chloride
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuum
  7. customIn this way the product was obtained with molecular weight 416.17 (C22H25FN2O5)

Sources & evidence

ORD record
ord-a97c7772dc6149feb9d3501c939816d1
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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