Acetic Acid → HCID 66910044, compound

HRID 2040600Notes

Reaction equation

HRID 2040600 reaction equation
[CH:1]([CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:7][CH:8]=2)=[O:2].[BH4-].[Na+].C(O)(=O)C>CO.O>[OH:2][CH2:1][CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:7][CH:8]=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86609778HCID 86609778, compound

Product 1

HCID 66910044HCID 66910044, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

9-Formyl-2,7-di(Boc-amino)fluorene (0.47 g, 1.1 mmol) was dissolved in anhydrous methanol (MeOH) (5 mL) under an argon atmosphere. NaBH4 (1.2 eq, 1.3 mmol, 0.05 g) was added and the reaction was stirred at room temperature for five hours. The reaction was diluted with deionized water and acidified to pH 5 with glacial acetic acid. The reaction was extracted with ethyl acetate (2×100 mL) and the organic layers were washed with saturated NaHCO3 (4×20 mL) and brine (3×20 mL). The organic layers were dried over MgSO4, filtered and evaporated. The crude product, orange solid, was purified by flash chromatography: silica gel 60 Å gradient elution 1-5% methanol in chloroform (alternative gradient elution with 15-20% ethyl acetate in dichloromethane). Product was a yellow solid (0.39, 83%). 1H-NMR (CD3OD): δ (ppm) 7.9 (s, 0.5H, NH urethane); 7.7 (s, 2H, Ar); 7.6 (d, 2H, Ar); 7.4 (d, 2H, Ar); 4.0 (m, 1H, CH); 3.9 (m, 2H, CH2); 1.6 (s, 18H, Boc).

Workup

  1. extractionThe reaction was extracted with ethyl acetate (2×100 mL)
  2. washthe organic layers were washed with saturated NaHCO3 (4×20 mL) and brine (3×20 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product, orange solid, was purified by flash chromatography
  7. washsilica gel 60 Å gradient elution 1-5% methanol in chloroform (alternative gradient elution with 15-20% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-647ed7e8693240bbb9839eef1d3dcf60
Source dataset
uspto-grants-2013_11
Patent number
US08580919B2

Reaction notes

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