Diethyl Ether → Tert-butyl 4-hydroxy-4-(pyridin-2-YL)piperidine-1-carboxylate

HRID 391117Notes

Reaction equation

HRID 391117 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[C:13]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][C:21]1=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CC[O:29]CC>>[C:16]([O:15][C:13]([N:20]1[CH2:25][CH2:24][C:23]([OH:29])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:22][CH2:21]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 79732-BromopyridineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 11948569Tert-butyl 4-hydroxy-4-(pyridin-2-YL)piperidine-1-carboxylate

Procedure

To a solution of nBuLi (2.5 m in hexanes, 2.00 mL) at −50° C. was added 2-bromopyridine (780 mg) in dry ether (10 mL). After 10 minutes an ethereal solution of BOC-piperidone (1.16 g) was added and the reaction mixture was gradually warmed to room temperature. After 1 hour, the reaction mixture was quenched with ammonium chloride solution, extracted with ether, dried (MgSO4) and the solvent removed in vacuo to yield an oil which was purified using flash chromatography to yield 4′-Hydroxy-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester. Cleavage of the BOC group with HCl yielded 2′,3′,5′,6′-tetrahydro-1′H-[2,4]bipyridinyl-4′-ol.

Workup

  1. customthe reaction mixture was quenched with ammonium chloride solution
  2. extractionextracted with ether
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto yield an oil which
  6. customwas purified

Sources & evidence

ORD record
ord-416ea12c7390417eb9094367e149754c
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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