2-Bromopyridine → 1-Boc-4-[(2-Bromopyridin-3-yl)hydroxymethyl]piperidine
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li+].CC([N-]C(C)C)C.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH:29]=[O:30])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH:29]([C:7]2[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[OH:30])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]Participants
5
Conditions
- Temperature
- -20 °C
Procedure
To a cold (−78° C.) solution of 2-bromo pyridine (800 mg, 5.06 mmol) in freshly distilled THF (15 mL) was added LDA (2.0 M, 2.8 mL, 6.5 mmol). The mixture was stirred under N2 for 30 min. A solution of 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.34 mmol) was added slowly to maintain the bath temperature below −70° C. The reaction was stirred at below −70° C. for 30 min, warmed to −20° C. within 60 min, and quenched with saturated aqueous NH4Cl (10 mL). Work-up and purification gave 4-[(2-bromo-pyridin-3-yl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (470 mg, 50%) as a colourless oil.
Workup
- temperatureto maintain the bath temperature below −70° C
- stirringThe reaction was stirred at below −70° C. for 30 min
- customquenched with saturated aqueous NH4Cl (10 mL)
- custompurification
Sources & evidence
- ORD record
- ord-0e832cd8b45b4888913d4fd157837816
- Source dataset
- uspto-grants-2009_02
- Patent number
- US07491735B2
Reaction notes
Loading…