Sodium Bicarbonate → HCID 58504109, compound

HRID 2407671Notes

Reaction equation

HRID 2407671 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:14]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C.C(=O)(O)[O-].[Na+]>C(#N)C.C(O)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:16][CH2:15]3)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2760465Ethyl 2-(piperidin-4-yl)acetateHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)

Product 1

HCID 58504109HCID 58504109, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of the compound prepared in Example 7 (500 mg), ethyl 2-(piperidin-4-yl)acetate (494 mg) and acetic acid (0.33 mL) in acetonitrile (15 mL) was stirred for 30 minutes at room temperature. Tetramethylammonium triacetoxyborohydride (2.28 g) was added and the reaction was stirred overnight. The reaction was poured into a saturated aqueous sodium bicarbonate solution and was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated to obtain the title compound (675 mg) having the following physical data.

Workup

  1. extractionwas extracted three times with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bd0ebdbb229544588e8e82dc77259143
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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