Methyl Ethyl Ketone → HCID 67220682, compound

HRID 603222Notes

Reaction equation

HRID 603222 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-fb415dab3e654f05ba4a8f7f4a277f42
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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