Sodium Hydroxide → HCID 10844509, compound

HRID 1885301Notes

Reaction equation

HRID 1885301 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 10632328HCID 10632328, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 10844509HCID 10844509, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.99 g of lithium aluminium hydride in 15 ml of tetrahydrofuran, a solution of 3.03 g of (2S,4R)-4-azido 2-ethoxycarbonyl-N-ethyl pyrrolidine in 10 ml of tetrahydrofuran was dropwise added while cooling and the combined was stirred for 1 hour. Sirring was continued at room temperature for additional 2 hours, and then a mixture of 4.7 ml of aqueous 1N-NaOH solution and 33 ml of tetrahydrofuran was added to decompose excess amount of lithium aluminium hydride. After filtrating the mixture to remove undissolved substance, the filtrate was concentrated under reduced pressure to obtain (2S,4R)-4-amino-N-ethyl-2-hydroxymethyl pyrrolidine as an oily product. Yield 1.33 g.

Workup

  1. temperaturewhile cooling
  2. waitSirring was continued at room temperature for additional 2 hours
  3. additionwas added
  4. filtrationAfter filtrating the mixture
  5. customto remove undissolved substance
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ac5aad9f75c64657811fe57e2e84ff59
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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