Acetic Acid → HCID 66991028, compound

HRID 454511Notes

Reaction equation

HRID 454511 reaction equation
[C:1](O)(=O)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:21]([O:28][C:29]1[CH:48]=[CH:47][C:46]([CH:49]2[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]2)=[CH:45][C:30]=1[C:31]([NH:33][C:34]1[CH:43]=[C:42]([Br:44])[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:48]=[CH:47][C:46]([CH:49]2[CH2:54][CH2:53][N:52]([CH3:1])[CH2:51][CH2:50]2)=[CH:45][C:30]=1[C:31]([NH:33][C:34]1[CH:43]=[C:42]([Br:44])[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 66990568HCID 66990568, compound

Product 1

HCID 66991028HCID 66991028, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.12 mL), a 37% aqueous solution of formaldehyde (0.10 mL), and sodium triacetoxyborohydride (0.54 g) were sequentially added to a tetrahydrofuran (5.4 mL) solution of the obtained methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-bromobenzoate (0.54 g), followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.48 g of methyl 2-(2-(benzyloxy)-5-(1-methylpiperidin-4-yl)benzamido)-4-bromobenzoate as a light yellow solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additiona saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-1c75b786c2784372a453e5f42e2e3d3d
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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