Isopropyl iodide → HCID 89924132, compound

HRID 626963Notes

Reaction equation

HRID 626963 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.I[CH:19]([CH3:21])[CH3:20].C[Si](C)(C)N[Si](C)(C)C.[Li]>C1COCC1>[CH:19]([C:4]1([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 89924132HCID 89924132, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (0.55 g, 2.26 mmol) and 2-iodopropane (0.32 mL, 3.2 mmol) in THF (2.5 mL) was stirred at −78° C. Lithium hexamethyldisilazane (3.2 mL, 3.2 mmol) was added, then the reaction mixture was allowed to warm to ambient temperature and stirred for 18 h. The reaction mixture was partitioned between diethyl ether and brine. The ether extract was dried (MgSO4), filtered and concentrated in vacuo, to give the title compound (0.54 g, 84%) as a pale yellow syrup, which was used without further purification. δH (400 MHz, DMSO-d6) 3.86 (m, 2H), 3.68 (m, 3H), 2.69 (m, 2H), 1.99 (m, 2H), 1.68 (m, 1H), 1.53 (m, 1H), 1.36 (s, 9H), 1.28 (m, 1H), 0.80 (d, J 6.9 Hz, 6H).

Workup

  1. customThe reaction mixture was partitioned between diethyl ether and brine
  2. extractionThe ether extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9380dc7b01f4abfbb9ce7d8b9ff60f3
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

Loading…