Acetic Acid → Methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoate

HRID 454574Notes

Reaction equation

HRID 454574 reaction equation
C=O.[C:3](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:21]([O:28][C:29]1[CH:53]=[CH:52][C:51]([CH:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)=[CH:50][C:30]=1[C:31]([NH:33][C:34]1[CH:43]=[C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:41]=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37])=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([O:28][C:29]1[CH:53]=[CH:52][C:51]([CH:54]2[CH2:55][CH2:56][N:57]([CH3:3])[CH2:58][CH2:59]2)=[CH:50][C:30]=1[C:31]([NH:33][C:34]1[CH:43]=[C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:41]=[CH:40][C:35]=1[C:36]([O:38][CH3:39])=[O:37])=[O:32])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66990546Methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate

Product 1

HCID 66990524Methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 37% formaldehyde aqueous solution (6.3 μL), acetic acid (0.022 mL), and sodium triacetoxyborohydride (0.10 g) were sequentially added to a tetrahydrofuran (3.0 mL) solution of methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate (0.10 g), followed by stirring at room temperature for 3 hours and 30 minutes. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 98-90% chloroform/methanol] to obtain 0.086 g of methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate and chloroform were added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography [eluent: 98-90% chloroform/methanol]

Sources & evidence

ORD record
ord-daf9194e54024d639228e48ccd7079f9
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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