Sodium borohydride → HCID 68711009, compound

HRID 2376301Notes

Reaction equation

HRID 2376301 reaction equation
[CH2:1]([NH:8][C:9]1[C:10]([CH3:22])=[CH:11][C:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[C:13]=2[C:20]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:8][C:9]1[C:10]([CH3:22])=[CH:11][C:12]2[O:16][C:15]([CH3:18])([CH3:17])[CH:14]([OH:19])[C:13]=2[C:20]=1[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23114206HCID 23114206, compound

Product 1

HCID 68711009HCID 68711009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(benzylamino)-2,2,4,6-tetramethyl-1-benzofuran-3 (2H)-one obtained in Reference Example 51 (8.5 g, 28.8 mmol) in methanol (20 mL) was added sodium borohydride (2.18 g, 57.6 mmol) at room temperature, and the mixture was stirred for 2 hours. The reaction solution was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the crude product, 5-(benzylamino)-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-3-ol. To a mixture of said compound with trifluoroacetic acid (30 mL) was added triethylsilane (10 mL, 64 mmol) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, and to the residue was added a saturated sodium hydrogen carbonate solution to alkalify the aqueous layer, which was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was crystallized with ethyl acetate-hexane to obtain 4.1 g (yield 51%) of the title compound. Melting point: 80-81° C. (ethyl acetate-hexane).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f6099043fa5492284d4a95514f18f06
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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