1-Benzyl-3-(trifluoroacetamido)pyrrolidine → 1-(Phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinamine

HRID 1884Notes

Reaction equation

HRID 1884 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27359931-Benzyl-3-(trifluoroacetamido)pyrrolidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 196914781-(Phenylmethyl)-N-(2,2,2-trifluoroethyl)-3-pyrrolidinamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 2.64 g sample of the compound from step 447a was added dropwise to a suspension of 1.11 g of LAH in ether stirred under N2 at 0° C. After one hour, the reaction was stirred at room temperature for 6 hours. The reaction was quenched by sequential addition of 1.2 mL of water, 1.2 mL of 15% NaOH and 2.4 mL of water. The mixture was filtered, and the filtrate was concentrated to give 2.39 of the title compound.

Workup

  1. stirringthe reaction was stirred at room temperature for 6 hours
  2. customThe reaction was quenched by sequential addition of 1.2 mL of water, 1.2 mL of 15% NaOH and 2.4 mL of water
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c6f52c74e1f4a55a7103d040ea32d13
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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