Acetic Acid → Methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

HRID 454725Notes

Reaction equation

HRID 454725 reaction equation
C(O)(=O)C.[Si:5]([O:12][CH2:13][CH:14]=O)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:30]([O:37][C:38]1[CH:62]=[CH:61][C:60]([CH:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)=[CH:59][C:39]=1[C:40]([NH:42][C:43]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:50]=[CH:49][C:44]=1[C:45]([O:47][CH3:48])=[O:46])=[O:41])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1>[CH2:30]([O:37][C:38]1[CH:62]=[CH:61][C:60]([CH:63]2[CH2:64][CH2:65][N:66]([CH2:14][CH2:13][O:12][Si:5]([C:8]([CH3:9])([CH3:10])[CH3:11])([CH3:6])[CH3:7])[CH2:67][CH2:68]2)=[CH:59][C:39]=1[C:40]([NH:42][C:43]1[CH:52]=[C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:50]=[CH:49][C:44]=1[C:45]([O:47][CH3:48])=[O:46])=[O:41])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66990546HCID 66990546, compound

Product 1

HCID 66990280Methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (0.023 mL), 2-(tert-butyldimethylsilyloxy)acetaldehyde (0.046 mL), and sodium triacetoxyborohydride (0.11 g) were sequentially added to a tetrahydrofuran (1.0 mL) solution of methyl 2-(2-(benzyloxy)-5-(piperidin-4-yl)benzamido)-4-phenylbenzoate (0.11 g), followed by stirring at room temperature for 13 hours. The solvent was evaporated under reduced pressure, and ethyl acetate was added to the residue. After removal of the insoluble substance by filtration, a saturated aqueous solution of sodium bicarbonate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol] to obtain 0.13 g of methyl 2-(2-(benzyloxy)-5-(1-(2-(tert-butyldimethylsilyloxy)ethyl)piperidin-4-yl)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. customAfter removal of the insoluble substance
  4. filtrationby filtration
  5. additiona saturated aqueous solution of sodium bicarbonate was added
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-92% chloroform/methanol]

Sources & evidence

ORD record
ord-0bb346795da84283941433040ecd29c1
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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