Ammonium Chloride → HCID 67313816, compound

HRID 1010899Notes

Reaction equation

HRID 1010899 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.[CH3:35][Mg]Cl.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:18]2[CH:19]=[CH:20][C:21]([C@@H:24]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:25])=[CH:22][CH:23]=2)([OH:34])[CH3:35])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67312805HCID 67312805, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 67313816HCID 67313816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

112 mg of the compound [22-1] was dissolved in 5 mL of tetrahydrofuran, and cooled to 0° C. Thereafter, 320 μL of methylmagnesium chloride (3.0M tetrahydrofuran solution) was added thereto, and the mixture was stirred for 1.5 hours while heating back to room temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the solution was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine 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 53 mg of benzyl-4-[1-(4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}phenyl)-1-hydroxyethyl]piperidine-1-carboxylate [22-2] (hereinafter, referred to as the compound [22-2]).

Workup

  1. temperaturewhile heating back to room temperature
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insolubles were filtered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70)

Sources & evidence

ORD record
ord-b79f1245913d4c9c8488905019f03d40
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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