Water → Ethyl 4-(4-aminophenyl)-1-benzoyl-3-pyrrolidinecarboxylate

HRID 1266459Notes

Reaction equation

HRID 1266459 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:9][N:8]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:7]1)=[O:5])[CH3:2].[Sn](Cl)(Cl)(Cl)Cl.O>C(OCC)(=O)C.C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([C:20](=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 24287Tin tetrachlorideHCID 53988865HCID 53988865, compound

Product 1

HCID 69832931Ethyl 4-(4-aminophenyl)-1-benzoyl-3-pyrrolidinecarboxylateYield 59.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 1-benzoyl-4-(4-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (10 g, Reference Example 9) in a mixture of ethyl acetate (324 ml) and ethanol (78 ml), at 24° C., was treated portionwise with tin chloride (30.65 g) then heated at 80° C. for 4 hours. After cooling to 24° C. the mixture was treated with water (400 ml), then with aqueous sodium bicarbonate solution (125 ml, 5%) and then filtered through a pad of celite washing twice with ethyl acetate (300 ml). The aqueous layer from the filtrate was separated and extracted twice with ethyl acetate (300 ml). The combined organic phases were dried over magnesium sulphate and evaporated (40° C. and 2.7 kPa). The residue was triturated with diethyl ether (100 ml) affording the title compound (5.48 g) as a white powder. 1H-NMR [250 MHz, (CD3)2SO at 373° K.]: δ 1.14 (t, J=7 Hz, 3H); 3.24 (m, 1H); 3.40 to 3.60 (m, 2H); 3.73 (dd, J=11 and 8.5 Hz, 1H); 3.80 to 4.00 (m, 2H); 4.08 (q, J=7 Hz, 2H); 6.58 (d, J=8 Hz, 2H); 6.98 (d, J=8 Hz, 2H); 7.40 to 7.60 (m, 5H).

Workup

  1. temperatureAfter cooling to 24° C. the mixture
  2. filtrationwith aqueous sodium bicarbonate solution (125 ml, 5%) and then filtered through a pad of celite
  3. washwashing twice with ethyl acetate (300 ml)
  4. customThe aqueous layer from the filtrate was separated
  5. extractionextracted twice with ethyl acetate (300 ml)
  6. dry with materialThe combined organic phases were dried over magnesium sulphate
  7. customevaporated (40° C. and 2.7 kPa)
  8. customThe residue was triturated with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-1a7762bb4f6c419197ac6479b3be82e6
Source dataset
uspto-grants-2003_04
Patent number
US06548533B2

Reaction notes

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