Potassium Hydroxide → 7-{4-[(2-Cyclopropyl-ethylamino)-methyl]-2-fluoro-phenoxy}-2,2-dimethyl-benzo[1,3]dioxin-4-one

HRID 1436322Notes

Reaction equation

HRID 1436322 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=3[F:22])=[CH:12][C:4]=2[O:3]1.[CH:24]1([CH2:27][CH2:28][NH2:29])[CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[K+]>ClCCCl>[CH:24]1([CH2:27][CH2:28][NH:29][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][C:11]3[CH:10]=[CH:9][C:5]4[C:6](=[O:8])[O:7][C:2]([CH3:1])([CH3:23])[O:3][C:4]=4[CH:12]=3)=[C:15]([F:22])[CH:16]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 10240761CyclopropaneethanamineHCID 579390354-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3-fluoro-benzaldehyde

Product 1

HCID 579390337-{4-[(2-Cyclopropyl-ethylamino)-methyl]-2-fluoro-phenoxy}-2,2-dimethyl-benzo[1,3]dioxin-4-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

4-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-yloxy)-3-fluoro-benzaldehyde (I-1b-1: 24.8 g) and 2-cyclopropyl-ethylamine (6.2 g) were combined in 1,2-dichloroethane (1.0 L). After stirring at ambient temperature for 1 hour, sodium triacetoxyborohydride (83 g) was added to the solution. After stirring overnight, the reaction mixture was treated with an aqueous 2 N potassium hydroxide solution, the organic phase was separated, dried over magnesium sulfate, filtered, and evaporated to provide the title compound (I-1c-2).

Workup

  1. stirringAfter stirring overnight
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b85b557429544d5386ee15ba6575e40a
Source dataset
uspto-grants-2009_11
Patent number
US07618996B2

Reaction notes

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