2-Bromopyridine → 2-(S)-Dibenzylamino-3-phenyl-1-pyridin-2-yl-propan-1-(S)-ol

HRID 1436483Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:13]([N:20]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C@@H:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:22]=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:31]([N:20]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C@@H:21]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C@@H:22]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[OH:23])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve 2-bromopyridine (2.73 mL, 28.63 mmol) in THF (150 mL) and cool to −78° C. Add n-butyllithium (12.0 mL, 2.5 M in hexanes). Slowly add 2-(S)-dibenzylamino-3-phenyl-propionaldehyde (4.71 g, 14.31 mmol) in THF (15 mL) and stir 30 min. Quench reaction with saturated aqueous ammonium chloride. Remove cold bath and warm to room temperature. Wash organic layer twice with 5% aqueous citric acid, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with dichloromethane and ethyl acetate) to give the title compound as a residue (3.654 g, 62%).

Workup

customQuench
customreaction with saturated aqueous ammonium chloride
customRemove cold bath
temperaturewarm to room temperature
dry with materialWash organic layer twice with 5% aqueous citric acid, saturated aqueous sodium chloride, dry (magnesium sulfate)
concentrationconcentrate
custompurify
wash(silica gel chromatography, eluting with dichloromethane and ethyl acetate)

Sources & evidence

ORD record: ord-a498cf77cac542bd874a0c4080a4d9a2
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07618978B2

Reaction notes

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