Methyl Ethyl Ketone → HCID 67220682, compound

HRID 2371179Notes

Reaction equation

HRID 2371179 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:25][C:26](=O)[CH2:27][CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C1COCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@H:19]3[O:24][CH2:23][CH2:22][N:21]([C@H:26]([CH3:25])[CH2:27][CH3:28])[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

8

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 57656789HCID 57656789, compound

Product 1

HCID 67220682HCID 67220682, compoundYield 13.1%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(3-chloro-4-fluorophenyl)-4-[(2R)-morpholin-2-ylmethyl]piperazine-1-carboxamide (300 mg, 0.84 mmol) and 2-butanone (0.16 ml, 1.12 mmol) in THF:DCM, 1:1 (8 ml), was added titanium tetraisopropoxide (1.99 ml, 6.72 mmol) and the reaction stirred at ambient temperature for 3 hours. Sodium tris-acetoxyborohydride (356 mg, 1.68 mmol) was added and the reaction stirred overnight. 2M NaOH was then added and the cloudy mixture filtered through celite. The filtrate was then extracted with EtOAc (×2), organics dried (Na2SO4), filtered and evaporated to a yellow oil. This was then purified by reverse phase HPLC using basic modifier to give the product as a yellow gum (42 mg, 0.11 mmol, 13% yield).

Workup

  1. stirringthe reaction stirred overnight
  2. filtrationthe cloudy mixture filtered through celite
  3. extractionThe filtrate was then extracted with EtOAc (×2)
  4. dry with materialorganics dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. customThis was then purified by reverse phase

Sources & evidence

ORD record
ord-8b8210c85a8843f4a9d5d39d04e54f76
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

Loading…