Aluminium lithium hydride → (2R,3S)-2-cyclopropylaminomethyl-pyrrolidin-3-ol

HRID 1359805Notes

Reaction equation

HRID 1359805 reaction equation
[CH:1]1([NH:4][C:5]([C@@H:7]2[C@@H:11]([OH:12])[CH2:10][CH2:9][NH:8]2)=O)[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O.[OH-].[Na+]>[CH:1]1([NH:4][CH2:5][C@@H:7]2[C@@H:11]([OH:12])[CH2:10][CH2:9][NH:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69998139(2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide

Product 1

HCID 69869847(2R,3S)-2-cyclopropylaminomethyl-pyrrolidin-3-olYield 25.6%

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S,3S)-3-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide (3.5 g, 20 mmol) and LAH (2.3 g, 3 eq.) in THF (50 mL) was heated to reflux for 2 hours. The cooled reaction was diluted with water (2.3 mL), a few drops of 10% NaOH, then water (2.3 mL). After stirring for 30 mins, the insolubles were filtered off, the filtrate was concentrated to give 0.8 g of (2R,3S)-2-cyclopropylaminomethyl-pyrrolidin-3-ol as a pale yellow oil. MS m/z 157 [M++1].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe cooled reaction
  4. filtrationthe insolubles were filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8577d067f9034795a98b04d9f7acfd29
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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