Iodoethane → HCID 117613432, compound

HRID 2167408Notes

Reaction equation

HRID 2167408 reaction equation
[CH2:1]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2][CH:3]([CH3:5])[CH3:4].[H-].[Na+].[H][H].I[CH2:19][CH3:20]>O1CCCC1.ClCCl>[CH2:19]([N:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[C:7](=[O:13])[O:8][C:9]([CH3:11])([CH3:10])[CH3:12])[CH3:20]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 17913132Tert-butyl iso-pentylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 117613432HCID 117613432, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl iso-pentylcarbamate (1.87 g, 9.99 mmol, 1.00 equiv) in tetrahydrofuran (10 mL) at 0° C. was added sodium hydride (600 mg, 25.00 mmol, 1.20 equiv). When the evolution of hydrogen subsided, iodoethane (1.7 g, 10.90 mmol, 1.10 equiv) was then added dropwise to the reaction mixture. The resulting solution was stirred at room temperature for 15 h. It was then diluted with 50 mL of dichloromethane and washed with 4×20 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-13% of ethyl acetate in petroleum ether to give 0.51 g (24%) of tert-butyl ethyl(iso-pentyl)carbamate as a yellow oil. 1H-NMR (300 MHz, CDCl3): δ 3.25-3.14 (m, 4H), 1.57-1.46 (m, 1H), 1.46 (s, 9H), 1.40-1.36 (m, 2H), 1.09 (t, J=7.2 Hz, 3H), 0.92 (d, J=8.8 Hz, 6H) ppm. LCMS (method D, ESI): RT=1.81 min, m/z=216.0 [M+H]+.

Workup

  1. washwashed with 4×20 mL of brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified on a silica gel column
  5. washeluted with 0-13% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-bbb95ae50eff4365852d6c867bfe2d68
Source dataset
uspto-grants-2015_06
Patent number
US09045455B2

Reaction notes

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