(6S)-4-benzyl-6-(4-fluorophenyl)morpholin-3-one → (S)-4-Benzyl-2-(4-fluorophenyl)morpholine

HRID 1671475Notes

Reaction equation

HRID 1671475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][N:12]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11](=O)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:9][CH2:10][CH2:11][N:12]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15982164(6S)-4-benzyl-6-(4-fluorophenyl)morpholin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 12002488(S)-4-Benzyl-2-(4-fluorophenyl)morpholineYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (6S)-6-(4-fluorophenyl)-4-(benzyl)morpholin-3-one (9.7 g) in tetrahydrofuran (30 ml) was added dropwise over 30 min to lithium aluminum hydride (2.6 g 70 mmol) in tetrahydrofuran (200 ml) at room temperature, and the reaction mixture was refluxed for 3 hrs. The reaction was quenched by addition of water (10.6 ml) and 15% aqueous sodium hydroxide solution (2.6 ml) at 0° C. The reaction mixture was filtered and the filtrate was concentrated to give (2S)-2-(4-fluorophenyl)-4-(benzyl)morpholine (9.05 g, yield 98% for 2 steps) as a colorless oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hrs
  2. customThe reaction was quenched by addition of water (10.6 ml) and 15% aqueous sodium hydroxide solution (2.6 ml) at 0° C
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b7e2e0c848124d019c0c8b1af1918605
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

Loading…