Water → (S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

HRID 2212042Notes

Reaction equation

HRID 2212042 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:12]([C@@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([CH2:12][C@@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13578534HCID 13578534, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineYield 59.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (87 ml, 87 mmol) was added dropwise to a solution of the crude (pyrrolidin-1-yl)-((S)-pyrrolidin-2-yl)methanone (4.89 g, 29 mmol) in tetrahydrofuran (90 ml). The reaction mixture was heated to reflux for 6 h. It was cooled to room temperature. Water (3.6 ml) was added carefully. A 1 N solution of sodium hydroxide (3.6 ml, 3.6 mmol) was added carefully. Water (10.7 ml) was added. The mixture was stirred for 1 h at room temperature. The precipitation was filtered off. The solvent was removed in vacuo to give 2.67 g of (S)-2-((pyrrolidin-1-yl)methyl)pyrrolidine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. customThe precipitation
  4. filtrationwas filtered off
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-46a39030b0ff42999d45e958f77682ca
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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