Sodium borohydride → 2-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-amino-3,4-dihydro-2H-1-benzopyran

HRID 582605Notes

Reaction equation

HRID 582605 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([C:24]([F:27])([F:26])[F:25])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>ClCCl.O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].[Pd]>[C:1]1([CH2:7][O:8][CH:9]([C:24]([F:27])([F:25])[F:26])[CH2:10][CH:11]2[CH2:16][CH2:15][C:14]3[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:13]=3[O:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 153456672-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran

Product 1

HCID 153456682-(2-Phenylmethoxy-3,3,3-trifluoropropyl)-6-amino-3,4-dihydro-2H-1-benzopyran

Reagents, catalysts & solvents 4

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.9 g (16 mmol) of 2-(2-phenylmethoxy-3,3,3-trifluoropropyl)-6-nitro-3,4-dihydro-2H-1-benzopyran in 50 ml of dichloromethane and 25 ml of water are added 73 mg of Adogen 464, 660 mg of 5% palladium on carbon containing 50% of water, and then a solution of 1.1 g (28 mmol) of sodium borohydride in 10 ml of water. The mixture is stirred for 1 hour, then it is filtered and the product is extracted with dichloromethane. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. By chromatography of the residue on a silica column using dichloromethane, 5.4 g of product are obtained.

Workup

  1. filtrationit is filtered
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customare obtained

Sources & evidence

ORD record
ord-1b566dc818c9494994e49402a8a392e0
Source dataset
uspto-grants-1999_07
Patent number
US05925662

Reaction notes

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