Triethylamine → 2,2-dimethyl-4-[N-(beta-trimethylsilylethanesulfonyl)-aminomethyl]-1,3-dioxolane

HRID 742532Notes

Reaction equation

HRID 742532 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][NH2:8])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:17][Si:18]([CH3:26])([CH3:25])[CH2:19][CH2:20][S:21](Cl)(=[O:23])=[O:22]>CN(C)C=O>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][NH:8][S:21]([CH2:20][CH2:19][Si:18]([CH3:26])([CH3:25])[CH3:17])(=[O:23])=[O:22])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 98370862-(Trimethylsilyl)ethane-1-sulfonyl chloride

Product 1

HCID 194262822,2-dimethyl-4-[N-(beta-trimethylsilylethanesulfonyl)-aminomethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2-dimethyl-4-aminomethyl-1,3-dioxolane (10.0 g, 0.08 mol) and triethylamine (8.1 g, 11.1 mL, 0.08 mol) in 100 mL of N,N-dimethylformamide is cooled to 0 C. under argon atmosphere. Then β-trimethylsilylethanesulfonyl chloride (16.0 g, 0.08 mol) is added dropwise. The solution is allowed to reach 25 C. and is stirred for 15 hours. The solvents are removed under reduced pressure and the crude residue is partitioned between dichloromethane (100 mL) and 5% sodium bicarbonate solution (50 mL). The layers are separated and the organic layer is dried over anhydrous sodium sulfate and evaporated to give 2,2-dimethyl-4-[N-(β-trimethylsilylethanesulfonyl)-aminomethyl]-1,3-dioxolane.

Workup

  1. customThe solvents are removed under reduced pressure
  2. customthe crude residue is partitioned between dichloromethane (100 mL) and 5% sodium bicarbonate solution (50 mL)
  3. customThe layers are separated
  4. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-4b2911baafe14fc485e2830d527b10aa
Source dataset
uspto-grants-1996_09
Patent number
US05554749

Reaction notes

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