tert-Butyl 3-[4-(ethoxycarbonyl)phenyl]-2,5-dihydro-1H-pyrrole-1-carboxylate → tert-Butyl 3-[4-(ethoxycarbonyl)phenyl]pyrrolidine-1-carboxylate

HRID 1891228Notes

Reaction equation

HRID 1891228 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H][H]>CCOC(C)=O.[Pt]=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13]2)=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 86644576tert-Butyl 3-[4-(ethoxycarbonyl)phenyl]-2,5-dihydro-1H-pyrrole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86644577tert-Butyl 3-[4-(ethoxycarbonyl)phenyl]pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of the title compound from Example 136 Step A (3.17 g, 9.99 mmol) in EtOAc (50 mL) was added platinum oxide (0.68 g, 3.00 mmol). The reaction flask was fitted with a hydrogen balloon attached to a 3-way adapter. The reaction mixture was then evacuated and back-filled with hydrogen. After this process was repeated three times, the reaction mixture was placed under a hydrogen atmosphere, and was stirred vigorously. After 45 min, the reaction mixture was filtered though Celite, rinsing with EtOAc. The mixture was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (0 to 8% EtOAc in hexanes, 8% EtOAc in hexanes, then 8 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 264.0 [M-t-Boc]+; 1H NMR (500 MHz, CDCl3) δ 7.99 (d, J=8.5 Hz, 2H), 7.30 (d, J=8.0 Hz, 2H), 4.37 (q, J=7.0 Hz, 2H), 3.92-3.76 (br m, 1H), 3.70-3.52 (br m, 1H), 3.48-3.34 (br m, 2H), 3.30 (t, J=10.0 Hz, 1H), 2.34-2.24 (br m, 1H), 1.99 (q, J=10.0 Hz, 1H), 1.48 (s, doubled (rotamers), 9H), 1.39 (t, J=7.0 Hz, 3H).

Workup

  1. customattached to a 3-way adapter
  2. customThe reaction mixture was then evacuated
  3. additionback-filled with hydrogen
  4. filtrationthe reaction mixture was filtered though Celite
  5. washrinsing with EtOAc
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography on silica gel (0 to 8% EtOAc in hexanes, 8% EtOAc in hexanes

Sources & evidence

ORD record
ord-946013cbc05e48bfba2086a09711a637
Source dataset
uspto-grants-2013_08
Patent number
US08507512B2

Reaction notes

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