Sodium borohydride → HCID 23082980, compound

HRID 920109Notes

Reaction equation

HRID 920109 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][CH:15]2[OH:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 224199626-(Benzyloxy)-2,3-dihydro-1H-inden-1-one

Product 1

HCID 23082980HCID 23082980, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of the product from Step A (44 g, 0.185 mol) in 500 mL of MeOH was added NaBH4 (7.1 g, 0.186 mol) in portions at 0° C. The mixture was allowed to warm to ambient temperature and stirred for 20 hours. The reaction mixture was concentrated and charged with 200 mL of aqueous NaOH (20%). The resulted mixture was extracted with EtOAc (200 mL×3). The combined organic extracts was washed with brine (200 mL×3), dried, and concentrated to give the title compound (32.0 g, 72%) as a white solid. 1H-NMR (600 MHz, CDCl3) δ 7.46-7.42 (m, 2H), 7.41-7.36 (m, 2H), 7.34-7.30 (m, 1H), 7.15 (d, J=8.2 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.2, 2.5 Hz, 1H), 5.20 (t, J=6.2 Hz, 1H), 5.07 (s, 2H), 3.01-2.95 (m, 1H), 2.79-2.72 (m, 1H), 2.55-2.47 (m, 1H), 2.01-1.87 (m, 1H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additioncharged with 200 mL of aqueous NaOH (20%)
  3. extractionThe resulted mixture was extracted with EtOAc (200 mL×3)
  4. washThe combined organic extracts was washed with brine (200 mL×3)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2d2285e4ccae46ab9f78fee86203e0ff
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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