Water → HCID 67313842, compound

HRID 1010901Notes

Reaction equation

HRID 1010901 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:34])[C:18]2[CH:23]=[CH:22][C:21]([C@@H:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:25])=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].O>O1CCCC1.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH:17]([C:18]2[CH:19]=[CH:20][C:21]([C@@H:24]([NH:26][C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH3:25])=[CH:22][CH:23]=2)[OH:34])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 67312805HCID 67312805, compound

Product 1

HCID 67313842HCID 67313842, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

267 mg of the compound [22-1] was dissolved in a mixed solvent of 10 mL of tetrahydrofuran and 1 mL of methanol, then 22 mg of sodium boronhydride was added thereto, and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine in that order, and dried over anhydrous magnesium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70), to obtain 256 mg of benzyl-4-[(4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)(hydroxy)methyl]piperidine-1-carboxylate [25-1] (hereinafter, referred to as the compound [25-1]).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70)

Sources & evidence

ORD record
ord-255b200adf414310a71e85b907f09f40
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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