Iodoethane → HCID 117613432, compound

HRID 59724Notes

Reaction equation

HRID 59724 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-7e681e9603224e869837f0c4497a4347
Source dataset
uspto-grants-2016_09
Patent number
US09440950B2

Reaction notes

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