Benzyl 1-benzylprolinate → (1-Benzylpyrrolidin-2-yl)methanol

HRID 1669447Notes

Reaction equation

HRID 1669447 reaction equation
[CH2:1]([N:8]1[CH2:22][CH2:21][CH2:20][C@H:9]1[C:10](OCC1C=CC=CC=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:22][CH2:21][CH2:20][CH:9]1[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11781411Benzyl 1-benzylprolinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 562951(1-Benzylpyrrolidin-2-yl)methanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (0.06M) of benzyl 1-benzylprolinate in THF was cooled in an ice bath and treated with LiAlH4 (3 eq). The resulting mixture was stirred at RT for 3 h, before being quenched by the addition of H2O. The resulting mixture was stirred at RT for 30 min and then filtered through a pad of Solka-Floc and the filtrate concentrated in vacuo. The crude was purified by FC (PE/EtOAc 6:4+1% NEt3) to afford the title compound as an off-white solid (62%). 1H NMR (400 MHz, CDCl3) 1.66-1.81 (m, 2H), 1.82-1.97 (m, 2H), 2.25-2.34 (m, 1H), 2.40-2.53 (m, 1H), 2.71-2.77 (m, 1H), 2.94-3.01 (m, 1H), 3.34-3.39 (m, 1H), 3.40-3.45 (m, 1H), 3.63-3.68 (m, 1H), 3.95-3.99 (m, 1H), 7.26-7.30 (m, 5H).

Workup

  1. custombefore being quenched by the addition of H2O
  2. stirringThe resulting mixture was stirred at RT for 30 min
  3. filtrationfiltered through a pad of Solka-Floc
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe crude was purified by FC (PE/EtOAc 6:4+1% NEt3)

Sources & evidence

ORD record
ord-f441ee5c54b14b43885f804270aa9bf6
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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