Aluminium lithium hydride → (S)-2-hydroxymethyl-1-(4-methoxyphenethyl)-2-methylpyrrolidine

HRID 1460485Notes

Reaction equation

HRID 1460485 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][C@@:10]2([CH3:17])[C:11](O)=[O:12])=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:12][CH2:11][C@:10]1([CH3:17])[CH2:14][CH2:15][CH2:16][N:9]1[CH2:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53946152HCID 53946152, compound

Product 1

HCID 53970712(S)-2-hydroxymethyl-1-(4-methoxyphenethyl)-2-methylpyrrolidineYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(4-Methoxyphenethyl)-2-methylproline (see Preparation 12) (895 mg) was added portionwise to a stirred suspension of lithium aluminium hydride (380 mg) in tetrahydrofuran (60 ml) and the mixture stirred at room temperature for 22 hours. The reaction was quenched by the cautious, dropwise, sequential addition of water (0.4 ml), 5M aqueous sodium hydroxide solution (0.4 ml) and water (1.2 ml), and then the resulting mixture filtered. The filtrate was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a colourless oil, (390 mg, 46%).

Workup

  1. customThe reaction was quenched by the cautious, dropwise,
  2. additionsequential addition of water (0.4 ml), 5M aqueous sodium hydroxide solution (0.4 ml) and water (1.2 ml)
  3. filtrationthe resulting mixture filtered
  4. dry with materialThe filtrate was dried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a2f764b4ee694d40afa8238cfaa30687
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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