Toluene → HCID 67797504, compound

HRID 728660Notes

Reaction equation

HRID 728660 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH:8]([NH:10][C:11](=[O:13])[CH3:12])[CH2:7][CH:6]=1)=O.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O.CO>[C:11]([NH:10][CH:8]1[CH2:9][C:5]([CH2:3][OH:2])=[CH:6][CH2:7]1)(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 9855836Potassium sodium tartarateHCID 19822736Methyl 4-(acetylamino)-1-cyclopentene-1-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 67797504HCID 67797504, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-70 °C

Procedure

(±)-Methyl-4-acetamido-1-cyclopentene-1-carboxylate (3.66 g, 20.0 mmol) was dried by evaporation of toluene giving a solution with a final volume of 50 mL. This solution was cooled to -70° C. under nitrogen. A solution of diisobutylaluminum hydride in toluene (1.5 M, 42 mL, 63 mmol) was added dropwise over 2 hours. The resulting hazy solution was stirred at -70° C. for an additional 40 minutes. Cold methanol (5 mL) was added dropwise, followed by a solution of sodium potassium tartrate (11.29 g) in water (15 mL) with the temperature maintained at -70° C. The resulting mixture was allowed to stir at 0° C. for several hours, diluted with methanol (150 mL) and filtered. The methanol was evaporated and the residual brown oil (3.44 g) chromatographed on silica gel. Title compound was eluted as pale yellow oil with 5% methanol-chloroform; 1.30 g (42%).

Workup

  1. temperaturemaintained at -70° C
  2. stirringto stir at 0° C. for several hours
  3. filtrationfiltered
  4. customThe methanol was evaporated
  5. customthe residual brown oil (3.44 g) chromatographed on silica gel
  6. washTitle compound was eluted as pale yellow oil with 5% methanol-chloroform

Sources & evidence

ORD record
ord-0053ce7fb2d2423f9b1dd2c0e3d2d7be
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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