Water → HCID 57949591, compound

HRID 2427527Notes

Reaction equation

HRID 2427527 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH:30]=[O:31])[CH:27]=[N:28][CH:29]=2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[BH4-].[Na+].O>C(O)C>[OH:31][CH2:30][C:26]1[CH:25]=[C:24]([C:4]2[CH:5]=[C:6]3[C:10](=[C:2]([CH3:1])[CH:3]=2)[C:9](=[O:11])[N:8]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:17][CH:18]=2)[CH2:7]3)[CH:29]=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 57949522HCID 57949522, compound

Product 1

HCID 57949591HCID 57949591, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindol-5-yl]-pyridine-3-carbaldehyde (91 mg, 0.212 mmol), in ethanol (10 mL) was added sodium borohydride (10 mg, 0.212 mmol). The mixture stirred for 4 hrs at room temperature and was poured into water and was extracted with ether. The organics were dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography eluting with 30-100% ethyl acetate in hexanes. The isolated product stirred in 1N HCl/MeOH overnight and was neutralized with 1N NaOH, extracted with ether, and concentrated to afford the title compound (62 mg, 68%) as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 8.74 (s, 1H), 78.61 (s, 1H), 8.15 (s, 1H), 7.41-7.36 (m, 4H), 7.22 (d, 2H), 4.91 (s, 2H), 4.82 (s, 2H), 4.36 (s, 2H), 2.85 (s, 3H).

Workup

  1. extractionwas extracted with ether
  2. dry with materialThe organics were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with 30-100% ethyl acetate in hexanes
  7. stirringThe isolated product stirred in 1N HCl/MeOH overnight
  8. extractionextracted with ether
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bd89ca279e454a45b70c3992b7fe2a2e
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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