Potassium bis(trimethylsilyl)amide → HCID 69060316, compound

HRID 736040Notes

Reaction equation

HRID 736040 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].C(OP(C[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([F:29])([F:28])[F:27])(=O)OCC)C.[CH2:30]([N:37]1[CH2:42][CH2:41][O:40][CH:39]([C:43]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=O)[CH2:38]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([N:37]1[CH2:42][CH2:41][O:40][CH:39]([CH:43]=[C:45]([C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:1]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]([F:27])([F:29])[F:28])[CH2:38]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 15818095Diethyl 2-(trifluoromethyl)benzylphosphonateHCID 179717622-Benzoyl-4-benzylmorpholine

Product 1

HCID 69060316HCID 69060316, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of KHMDS (0.5M in toluene, 50 ml, 25 mmol) at 0° C. in dry tetrahydrofuran (70 ml) under nitrogen is added freshly prepared neat (2-trifluoromethyl-benzyl)-phosphonic acid diethyl ester (5.7 ml, 25 mmol, 1 equiv.). The reaction is warmed to room temperature over 1 hour and then racemic (4-benzyl-morpholin-2-yl)-phenyl-methanone (7 g, 25 mmol in 25 ml of dry tetrahydrofuran) is added dropwise. The reaction is left at room temperature and stirred for 2 hours. At the end of this time the reaction solvent is removed under reduced vacuum 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. The resulting residue is purified by column chromatography on silica gel to yield a colourless oil (6.5 g, 61%).

Workup

  1. waitThe reaction is left at room temperature
  2. customAt the end of this time the reaction solvent is removed under reduced vacuum
  3. customto quenching with water
  4. extractionAfter extraction with diethyl ether
  5. dry with materialdrying (MgSO4) the solvent
  6. customis again removed under reduced pressure
  7. customThe resulting residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d14eb0f5b5224268a73f170ce176cb34
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

Loading…