HCID 18661335, compound → HCID 9904942, compound

HRID 370363Notes

Reaction equation

HRID 370363 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@@H:13]([N:15](C(O)=O)[CH2:16]C2C=CC=CC=2)[CH3:14])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1.CCOCC>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@@H:13]([NH:15][CH3:16])[CH3:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18661335HCID 18661335, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9904942HCID 9904942, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(S,S)-1-benzyl-2-oxo-3-[1'-(carboxybenzylamino)ethyl]pyrrolidine (0.51 g, 1.44 mmol) is dissolved in tetrahydrofuran (20 ml) under a N2 atmosphere. LAH (0.32 g, 8.43 mmol) is added and the reaction mixture is refluxed for 12 hours. The reaction mixture is cooled to 0° C., diluted with Et2O and quenched with 15% aqueous NaOH. The resulting mixture is filtered through a celite pad which is then washed carefully with Et2O. The filtrate is washed with 15% aqueous NaOH and the aqueous layer extracted with Et2O. The combined Et2O layers are dried over MgSO4, filtered and concentrated under a stream of N2 to give crude (R,S)-1-benzyl-3-[1'-(methylamino)ethyl]pyrrolidine: 1H NMR (300 MHz, CDCl3) δ 1.04 (d, J is 6 Hz, 3H), 1.52 (m, 1H), 1.93 (m, 1H), 2.17 (m, 1H), 2.25 (dd, J is 16, 8 Hz, 1H), 2.37 (s, 3H), 2.33-2.49 (m, 2H), 2.56 (dd, J is 15, 8 Hz, 1H), 2.77 (dd, J is 8, 8 Hz, 1H), 3.58 (d, J is 12.8 Hz, 1H), 3.60 (d, J is 12.8 Hz, 1H), 7.23-7.36 (m, 5H). This crude material is suitable for use in Step 5.

Workup

  1. temperaturethe reaction mixture is refluxed for 12 hours
  2. customquenched with 15% aqueous NaOH
  3. filtrationThe resulting mixture is filtered through a celite pad which
  4. washis then washed carefully with Et2O
  5. washThe filtrate is washed with 15% aqueous NaOH
  6. extractionthe aqueous layer extracted with Et2O
  7. dry with materialThe combined Et2O layers are dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under a stream of N2

Sources & evidence

ORD record
ord-de30b2c7cb1e47f5a2fd476074c6d9a8
Source dataset
uspto-grants-2000_10
Patent number
US06140510

Reaction notes

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