Water → HCID 131729007, compound

HRID 1010895Notes

Reaction equation

HRID 1010895 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=[O:30].O>O1CCCC1>[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:29]([OH:30])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=2)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 131729007HCID 131729007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

500 mg of the compound [1-1] was dissolved in 10 mL of tetrahydrofuran and cooled to −78° C. Thereafter, 2.33 mL of n-butyllithium (1.57M hexane solution) was added thereto. After the 1 hour stirring at the same temperature, 193 μL of picolinaldehyde was added to the resulting white suspension, and the suspension was stirred overnight while heating back to room temperature. 50 mL of water was added to the reaction mixture, and the mixture was extracted with 200 mL of ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. Then, the insolubles were filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70) to obtain 212 mg of tert-butyl((1S)-1-{4-[hydroxy (pyridin-2-yl)methyl]phenyl}ethyl)carbamate [12-1] (hereinafter, referred to as the compound [12-1]) as a light brown oily product.

Workup

  1. additionwas added to the resulting white suspension
  2. temperaturewhile heating back to room temperature
  3. extractionthe mixture was extracted with 200 mL of ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThen, the insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0-30/70)

Sources & evidence

ORD record
ord-95b253144d314623a6002e6cd0dd629e
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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