Potassium bis(trimethylsilyl)amide → 4-Benzyl-2-(1,2-diphenyl-vinyl)-morpholine

HRID 736036Notes

Reaction equation

HRID 736036 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=O)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 179717622-Benzoyl-4-benzylmorpholine

Product 1

HCID 689010384-Benzyl-2-(1,2-diphenyl-vinyl)-morpholine

Procedure

To a cooled solution of KHMDS (0.5M in toluene, 40 ml, 20 mmol) at 0° C. under nitrogen is added diethyl benzyl phosphonate (available from Aldrich Chemical Company) (4. 1 ml, 19.7 mmol). The reaction is held at this temperature and stirred for 30 minutes then warmed to room temperature and after 10 minutes a solution of racemic (4-benzyl-morpholin-2-yl)-phenyl-methanone (5.03 g, 17.9 mmol in 25 ml of dry tetrahydrofuran) is added dropwise and the reaction allowed to stir for 30 minutes. At the end of this time the reaction solvent is removed under reduced pressure and replaced with diethyl ether prior to quenching with water. After extraction with diethyl ether and drying (MgSO4) the solvent is again removed under reduced pressure and replaced with methanol at which point a white precipitate forms. The solution is filtered and the cake washed with cold methanol and air-dried. The methanolic solution is further purified using SCX-2 chromatography followed by silica gel chromatography to provide the required material, which is combined with the white precipitate previously obtained.

Workup

  1. additionis added dropwise
  2. stirringto stir for 30 minutes
  3. customAt the end of this time the reaction solvent is removed under reduced pressure
  4. customto quenching with water
  5. extractionAfter extraction with diethyl ether
  6. dry with materialdrying (MgSO4) the solvent
  7. customis again removed under reduced pressure
  8. filtrationThe solution is filtered
  9. washthe cake washed with cold methanol
  10. customair-dried
  11. customThe methanolic solution is further purified

Sources & evidence

ORD record
ord-faa372f5f5c349f48e64a1407eea4243
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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