Water → HCID 20036392, compound

HRID 1904915Notes

Reaction equation

HRID 1904915 reaction equation
[C:1]1([C:7]2([C:19]([NH2:21])=O)[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([C:7]2([CH2:19][NH2:21])[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 14476560HCID 14476560, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20036392HCID 20036392, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.1 g (0.011 mol) of 3-phenyl-1-(phenylmethyl)-3-pyrrolidinecarboxamide in 150 ml of dry tetrahydrofuran was added 0.84 g (0.022 mol) of lithium aluminum hydride in portions under argon. The suspension was stirred overnight at room temperature. To the mixture was added 0.7 ml of water, 0.9 ml of 40% sodium hydroxide, and 3.0 ml of water. The grainy precipitate was filtered, and the filtrate was concentrated to give 2.9 g of 3-phenyl-1-(phenylmethyl)-3-pyrrolidinemethanamine. A solution of the residue from the above reaction, 0.5 g of 20% palladium on carbon, and 100 ml of methanol was shaken in an atmosphere of hydrogen at 50 psi for 18 hours. The catalyst was filtered and the filtrate concentrated to give 1.8 g of the title compound.

Workup

  1. filtrationThe grainy precipitate was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-efdc5d31b8484f249a525608d2367206
Source dataset
uspto-grants-1989_06
Patent number
US04840956

Reaction notes

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