Triethylamine → Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate

HRID 222272Notes

Reaction equation

HRID 222272 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][NH:9][CH3:10].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19](Cl)=[O:20])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[O:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][N:9]([CH3:10])[C:19](=[O:20])[O:18][CH2:17][C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 66972118(1,4-Dioxan-2-ylmethyl)methylamine hydrochloride

Product 1

HCID 66972115Benzyl (1,4-dioxan-2-ylmethyl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(1,4-dioxan-2-yl)-N-methylmethanamine hydrochloride (4.83 g, 29 mmol) was dissolved in 100 mL dichloromethane. Benzyl chloridocarbonate (4.9 mL, 35 mmol) and triethylamine (10 mL, 72 mmol) were added. The solution was stirred at ambient temperature. After 12 hours, the solution was concentrated, then diluted with ethyl acetate, and washed with saturated sodium bicarbonate and water. The organic layer was separated, dried with magnesium sulfate, filtered, concentrated in vacuo, and purified by silica chromatography (0-100% ethyl acetate/hexanes gradient) to afford the title compound (racemic mixture).

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and water
  4. customThe organic layer was separated
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by silica chromatography (0-100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-74cd015d7ab64ec8b68ba742486339f8
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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