2-(1-((Tert-butoxy)carbonyl)piperidin-3-yl)acetic acid → 206989-47-1

HRID 277884Notes

Reaction equation

HRID 277884 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15]([OH:17])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li][CH3:19]>CCOCC>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][C:15](=[O:17])[CH3:19])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 41150282-(1-((Tert-butoxy)carbonyl)piperidin-3-yl)acetic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 12017165206989-47-1

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-2 (13.4 g, 55 mmol) in ether (500 mL) at 0° C. was treated dropwise with MeLi (87 mL, 121 mmol; 1.4 M/ether). After addition was complete, the cooling bath was removed and the reaction mixture was stirred overnight. The reaction mixture was then poured into an ice/water mixture and then extracted with ether. The ether extracts were washed with brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 30% EtOAc/hexanes) gave 2-3 as a colorless oil.

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. additionThe reaction mixture was then poured into an ice/water mixture
  4. extractionextracted with ether
  5. washThe ether extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7fd41e6c4e64bae9634c964c438b1d3
Source dataset
uspto-grants-2002_03
Patent number
US06358970B1

Reaction notes

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