3-Bromopyridine → HCID 68972594, compound

HRID 1726143Notes

Reaction equation

HRID 1726143 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=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[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[Br:1])[OH:30])[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 122863-BromopyridineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 68972594HCID 68972594, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a cold (−90° C.) solution of 3-bromo pyridine (741 mg, 4.7 mmol) in freshly distilled THF (18 ml) was added LDA (2.0M, 2.6 mL, 5.2 mmol). The mixture was stirred under N2 for 20 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 −80° C. The reaction was continued at below −80° C. for 30 min, warmed to −20° C. within 30 min and quenched with saturated aqueous NH4Cl (10 mL). Work-up and purification gave 4-[(3-bromo-pyridin-4-yl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (610 mg, 70%) as colourless oil.

Workup

  1. temperatureto maintain the bath temperature below −80° C
  2. waitThe reaction was continued at below −80° C. for 30 min
  3. customquenched with saturated aqueous NH4Cl (10 mL)
  4. custompurification

Sources & evidence

ORD record
ord-906571b1f8ef407fb4e2588a587d2b56
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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