Tetrahydrofuran → 1-{[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methyl}piperidine

HRID 1366696Notes

Reaction equation

HRID 1366696 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11]C[C@H:9]2[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:27]1COCC1>>[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH2:11][C@H:9]2[CH2:14][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:27]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 66936271(2S)-1-(phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidine

Product 1

HCID 669367461-{[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methyl}piperidineYield 83%

Conditions

Temperature
0 °C

Procedure

(2S)-1-(Phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidine (901 mg, 3.307 mmol) was dissolved in 20 mL of THF, cooled to 0° C., and then LiAlH4 (251 mg, 6.615 mmol) was added portion wise. The mixture was heated to 80° C. for 2 h, then allowed to cool to RT. The reaction was quenched in succession with H2O (0.300 mL), 15% aq. NaOH (0.300 mL) and H2O (0.900 mL) and was stirred at room temperature overnight. The contents were filtered, and the filtrate was concentrated in vacuo to provide 1-{[(2S)-1-(phenylmethyl)-2-pyrrolidinyl]methyl}piperidine (710 mg, 83%).

Workup

  1. temperatureThe mixture was heated to 80° C. for 2 h
  2. temperatureto cool to RT
  3. customThe reaction was quenched in succession with H2O (0.300 mL), 15% aq. NaOH (0.300 mL) and H2O (0.900 mL)
  4. filtrationThe contents were filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e028d93b8b4c4578bcb3a5208b7efd03
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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