Ammonium Acetate → HCID 67975592, compound

HRID 1844085Notes

Reaction equation

HRID 1844085 reaction equation
C([O-])(=O)C.[NH4+].C[O:7][C:8](=O)[CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O.C([BH3-])#[N:22].[Na+]>CO>[NH:22]1[C:8](=[O:7])[CH2:9][CH:10]2[CH2:18][C:17]3[C:12]([CH:11]12)=[CH:13][CH:14]=[CH:15][CH:16]=3

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 589496HCID 589496, compoundHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67975592HCID 67975592, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ammonium acetate (3.77 g, 48.9 mmol) was coevaporated in anhydrous methanol. Then, (1-Oxo-indan-2-yl)-acetic acid methyl ester H1 (1.00 g, 4.89 mmol) in methanol (40 mL) was added followed by molecular sieves (4.9 g). The solution was stirred for 30 min and sodium cyanoborohydride (0.92 g, 14.9 mmol) was added. The suspension was refluxed for 40 h. The solution was filtered through celite. A saturated solution of sodium hydrogenocarbonate was added and the solution was extracted with ethyl acetate (3*50 mL). The combined organic layers were washed with hydrogen chloride (1N), brine, dried and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate and then ethyl acetate/methanol (95/5) to give 3,3a,4,8b-tetrahydro-1H-indeno[1,2-b]pyrrol-2-one G1 (White solid, 300 mg, 35%). LCMS (method A) RT 1.17; ES 196, 174; IR 3233, 1689 cm−1; Mp: 150-153° C.; 1H NMR (400 MHz, CD3OD) δ 7.34 (1H, d), 7.12-7.27 (3H, m), 5.04 (1H, d), 3.22-3.37 (2H, m), 2.83 (1H, d), 2.70 (1H, dd), 2.15 (1H, dd) ppm.

Workup

  1. temperatureThe suspension was refluxed for 40 h
  2. filtrationThe solution was filtered through celite
  3. additionA saturated solution of sodium hydrogenocarbonate was added
  4. extractionthe solution was extracted with ethyl acetate (3*50 mL)
  5. washThe combined organic layers were washed with hydrogen chloride (1N), brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c3afc34feb5346fe8e4f844ac42b32f1
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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