p-Toluenesulfonic acid → 1,3-Dioxolane-4-methanamine, 2,2-dimethyl-

HRID 708193Notes

Reaction equation

HRID 708193 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][OH:5].[C:7]1(C)[CH:12]=CC(S(O)(=O)=O)=C[CH:8]=1>C(OC(C)=O)C.Cl.COC(OC)(C)C>[CH3:8][C:7]1([CH3:12])[O:6][CH:3]([CH2:2][NH2:1])[CH2:4][O:5]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 735613-Amino-1,2-propanediol

Product 1

HCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-Yield 533.6%

Reagents, catalysts & solvents 2

HCID 64952,2-DimethoxypropaneSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

3-Aminopropane-1,2-diol (400 mg, 4.4 mmol) was dissolved in EtOAc—HCl (20 mL). And the reaction mixture was stirred at r.t. for 30 min. The reaction mixture was concentrated in vacuo to get to the white solid. The white solid was added in 2,2-dimethoxy-propane (10 mL) and toluene-4-sulfonic acid (86 mg, 0.5 mmol) was added into the mixture. The reaction mixture was stirred at 60° C. for 12 h. The reaction mixture was concentrated in vacuo, washed by acetone to give (2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (350 mg, yield: 46%). 1HNMR (DMSO-d6, 400 MHz): δ8.08 (s, 2H), 4.32 (s, 1H), 4.05 (q, J=4.8 Hz, 1H), 3.73 (t, J=6.4 Hz, 1H), 3.00-2.78 (m, 2H), 1.37 (s, 3H), 1.28 (s, 3H)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto get to the white solid
  3. stirringThe reaction mixture was stirred at 60° C. for 12 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washwashed by acetone

Sources & evidence

ORD record
ord-1d5d873715864deb83de356fc34e1d49
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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