Sodium Hydroxide → HCID 10701943, compound

HRID 1885306Notes

Reaction equation

HRID 1885306 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([C@@H:10]1[CH2:14][N:13]([CH2:15][CH3:16])[C@H:12]([C:17](OCC)=[O:18])[CH2:11]1)=[N+]=[N-].[OH-].[Na+]>O1CCCC1>[NH2:7][C@@H:10]1[CH2:14][N:13]([CH2:15][CH3:16])[C@H:12]([CH2:17][OH:18])[CH2:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10751025HCID 10751025, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 10701943HCID 10701943, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.41 g of lithium aluminium hydride were suspended in 10 ml of tetrahydrofuran and while cooling, a solution of 1.9 g of (2S,4S)-4-azido-2-ethoxycarbonyl-N-ethyl pyrrolidine in 4 ml of tetrahydrofuran was dropwise added thereto. After stirring at the same temperature for 1 hour, the temperature of reaction mixture was raised to room temperature and the mixture was stirred for 2 hours. To this, a mixture of 1 ml of 1N-NaOH solution and 9 ml of tetrahydrofuran was added to decompose lithium aluminium hydride and undissolved material was filtered. The filtrate was concentrated under reduced pressure to obtain (2S,4S)-4-amino-N-ethyl2-hydroxymethyl pyrrolidine. Yield 1.05 g.

Workup

  1. temperaturewhile cooling
  2. customthe temperature of reaction mixture
  3. stirringthe mixture was stirred for 2 hours
  4. additionwas added
  5. filtrationwas filtered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2efc86d559c423fadda6d4158b3d1b9
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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