Cyclobutanone → HCID 67322891, compound

HRID 1257639Notes

Reaction equation

HRID 1257639 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7].[C:9]1(=O)[CH2:12][CH2:11][CH2:10]1>CO.[Pd]>[CH:9]1([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[C:6]([OH:8])=[O:7])[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 14496CyclobutanoneHCID 145742L-Proline

Product 1

HCID 67322891HCID 67322891, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-pyrrolidine-2-carboxylic acid (1.0 g, 8.69 mmol), cyclobutanone (671 mg, 9.56 mmol) and 10% Pd/C (44 mg) in MeOH (10 mL) was stirred under an atmosphere of hydrogen for 20 hours. The reaction mixture was filtered through Celite® and the filtrate concentrated under vacuum. The resulting residue was triturated with diethyl ether to afford (S)-1-cyclobutyl-pyrrolidine-2-carboxylic acid. 1H NMR (300 MHz, CDCl3) δ: 4.41 (s, 1H), 3.86 (dt, 1H), 3.78-3.63 (m, 2H), 2.78 (m, 1H), 2.55 (m, 1H), 2.57-2.09 (m, 4H), 1.91 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3a8fb144c0c14b47b6a6e7412215b6f0
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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