Boron trifluoride → 2-[3-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-hydroxymethyl-4,5-dihydro-isoxazol-5-yl]-ethanol

HRID 1169850Notes

Reaction equation

HRID 1169850 reaction equation
[BH4-].[Na+].[C:3]([CH2:6][C:7]1([C:26](O)=[O:27])[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH:13]=2)[CH2:8]1)(O)=[O:4].FB(F)F.[OH-].[Na+]>O1CCCC1.C(OC(=O)C)C.O>[CH:21]1([O:20][C:14]2[CH:13]=[C:12]([C:9]3[CH2:8][C:7]([CH2:6][CH2:3][OH:4])([CH2:26][OH:27])[O:11][N:10]=3)[CH:17]=[CH:16][C:15]=2[O:18][CH3:19])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

8

Reactant 4

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 595509785-(Carboxymethyl)-3-[3-(cyclopentyloxy)-4-methoxyphenyl]-4,5-dihydroisoxazole-5-carboxylic acid

Product 1

HCID 686838572-[3-(3-Cyclopentyloxy-4-methoxy-phenyl)-5-hydroxymethyl-4,5-dihydro-isoxazol-5-yl]-ethanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium borohydride (3 eq) in tetrahydrofuran, was added a solution of the compound obtained from step d above (1 eq) in tetrahydrofuran. To the resulting reaction mixture was added ethereal solution of trifluoroborane (3 eq) at 0° C. and stirred for 14-16 hours at ambient temperature. Sodium hydroxide (1N) solution was added at 0° C. and stirred for 1 hour. The reaction mixture was diluted with ethylacetate and water. The combined extract was washed with saturated solution of sodium chloride and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound.

Workup

  1. customTo the resulting reaction mixture
  2. stirringstirred for 1 hour
  3. extractionThe combined extract
  4. washwas washed with saturated solution of sodium chloride
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c7d61dad990043cbb6fce1030158b9e7
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

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