2-Allylamino-1-(3-(s)-hydroxy-pyrrolidin-1-yl)-2-(s)-phenyl-ethanone → HCID 20756538, compound

HRID 23587Notes

Reaction equation

HRID 23587 reaction equation
[CH2:1]([NH:4][C@@H:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)=O)[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([NH:4][C@@H:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 207565392-Allylamino-1-(3-(s)-hydroxy-pyrrolidin-1-yl)-2-(s)-phenyl-ethanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 20756538HCID 20756538, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-allylamino-1-(3-(S)-hydroxy-pyrrolidin-1-yl)-2-(S)-phenyl-ethanone (5.65 g, 15.1 mmol) in anhydrous tetrahydrofuran (60 cm3) cooled to 0° C. in an ice bath was added a 1 M solution of lithium aluminum hydride (22.6 cm3, 22.7 mmol) over 20 minutes. The solution was allowed to warm and stir at ambient temperature for 16 hours. The reaction was cooled to 0° C. in an ice bath and quenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3) to form a white flocculate precipitate. The mixture was vacuum filtered, the precipitate washed with tetrahydrofuran (5×30 cm3) and the filtrate volatile fractions removed in vacuo to afford a crude yellow oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1) to afford the title compound as a yellow viscous oil (2.54 g, 68.3%) with a positive ion ESI (M+H)+247.2.

Workup

  1. temperatureto warm
  2. temperatureThe reaction was cooled to 0° C. in an ice bath
  3. customquenched with water (0.860 cm3), 15% sodium hydroxide (0.860 cm3) and water (2.60 cm3)
  4. customto form a white flocculate precipitate
  5. filtrationfiltered
  6. washthe precipitate washed with tetrahydrofuran (5×30 cm3)
  7. customthe filtrate volatile fractions removed in vacuo
  8. customto afford a crude yellow oil
  9. customThe crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol-ammonium hydroxide 97:3:0 to 90:10:1)

Sources & evidence

ORD record
ord-610a9013493f4ad29eda5f303f2c0eda
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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