Ammonium Acetate → HCID 54187452, compound

HRID 480195

Reaction equation

HRID 480195 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:36].[Na+]>CO>[NH2:36][CH2:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C:12]([N:14]1[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

Product 1

HCID 54187452HCID 54187452, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,5S)-5-chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (1.86 g, 4.44 mmol) in MeOH (20 mL) was added ammonium acetate (3.42 g, 44 mmol) and sodium cyanoborohydride (0.195 g, 3.1 mmol). The resulting mixture was stirred overnight at ambient temperature. The reaction was quenched with concentrated hydrochloric acid and concentrated in vacuo. The residue was dissolved in water and basified with aqueous 3N NaOH (pH>10). The product was extracted with dichloromethane (2×) and ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.29 g, 69% yield)

Workup

  1. customThe reaction was quenched with concentrated hydrochloric acid
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water and basified with aqueous 3N NaOH (pH>10)
  4. extractionThe product was extracted with dichloromethane (2×) and ethyl acetate (2×)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4ef7363554341ffa01d88267800552d
Source dataset
uspto-grants-2003_11
Patent number
US06649611B2

Linked notes

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