2,2,6,6-Tetramethylpiperidine → HCID 178418821, compound

HRID 577848Notes

Reaction equation

HRID 577848 reaction equation
C([Li:5])CCC.[CH3:6][C:7]1([CH3:15])[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[NH:8]1>C1COCC1>[Li:5][N:8]1[C:9]([CH3:14])([CH3:13])[CH2:10][CH2:11][CH2:12][C:7]1([CH3:15])[CH3:6]

Participants

4

Reactant 2

HCID 130352,2,6,6-TetramethylpiperidineHCID 178418339Butyllithium

Product 1

HCID 178418821HCID 178418821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyllithium, 2.5M in hexanes (1.718 mL, 4.30 mmol) was added dropwise to a solution of 2,2,6,6-tetramethylpiperidine (0.802 mL, 4.73 mmol) in 15 ml THF at −78° C. The flask was removed from the −78° C. bath, and stirred at ca 0° C. for 10 minutes, then recooled to −78° C. to give a pale yellow solution of LiTMP. A solution of (2R,6S)-4-[6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-chloro-3-fluorophenyl]-2,6-dimethylmorpholine (Intermediate 42, 1.1 g, 2.15 mmol) 20 ml THF was cannulated into the LiTMP solution to give a yellow solution which was stirred at −78 for about 1 hour; then N-methoxy-N-methylpyrazine-2-carboxamide (1.077 g, 6.44 mmol) was added. The mixture was stirred at −78° C. After 5 hours the reaction was worked up by adding saturated NH4Cl to the −78° C. solution and extracting with EtOAc (3×). After drying over MgSO4, concentration of the mixture gave material that was purified on SiO2 using 0-10% acetone/hexanes to recover 891 mg (67%) of the title compound as a yellow oil.

Workup

  1. customThe flask was removed from the −78° C. bath
  2. customrecooled to −78° C.

Sources & evidence

ORD record
ord-8a67d8f4f7c140b8b1a4d9f1e7603b6f
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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