Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate → [1-Benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanol

HRID 712437Notes

Reaction equation

HRID 712437 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13](OC)=[O:14])[CH:10]([C:17](OC)=[O:18])[CH2:9]1)[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[CH2:12][CH:11]([CH2:13][OH:14])[CH:10]([CH2:17][OH:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13120109Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13814311[1-Benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanolYield 77.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate (0.50 g) in THF (20 mL) was added LiAlH4 (3.0 eq) at 0° C. under N2. The reaction mixture was heated to the room temperature and stirred for 24 h. The reaction was quenched with water, 10% NaOH and water in turn. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH) to give the title compound (0.31 g, 63.79%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 222.3 (M+1).

Workup

  1. customThe reaction was quenched with water, 10% NaOH and water in turn
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-cbd3b39ce198474bb137e2560003cb14
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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