Dimethoxymethane → HCID 18977225, compound

HRID 2393761Notes

Reaction equation

HRID 2393761 reaction equation
[C:1]1([CH3:21])[C:2]([S:7]([NH:10][C:11]([CH3:20])([CH3:19])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[B].[CH3:23]OCOC>>[C:1]1([CH3:21])[C:2]([S:7]([N:10]2[C:11]([CH3:19])([CH3:20])[CH2:12][C:13]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:23]2)(=[O:8])=[O:9])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 8020DimethoxymethaneHCID 5462311BoronHCID 18977226HCID 18977226, compound

Product 1

HCID 18977225HCID 18977225, compoundYield 99%

Procedure

To a nitrogen-blanketed mixture of N-toluenesulfonyl-1,1-dimethyl-2-phenyl-ethylamine (8.30 g, 0.027 mol.) in dimethoxymethane (50 mL) was added boron trifluororo etherate (BF3 ·OEt2, 9.9 mL, 0.081 mol.). The mixture was stirred at room temperature for 12 hours while monitoring by gas chromatography. The reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL), separated, and the organic layer is washed with saturated sodium bicarbonate (2×100 mL) and dried over sodium sulfate (Na2 SO4). The drying agent was filtered off and the filtrate was concentrated at 40°/50 torr to give 8.55 g of N-toluenesulfonyl-3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline (yield=99%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (100 mL) and water (100 mL)
  2. customseparated
  3. washthe organic layer is washed with saturated sodium bicarbonate (2×100 mL)
  4. dry with materialdried over sodium sulfate (Na2 SO4)
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated at 40°/50 torr

Sources & evidence

ORD record
ord-aaf35b3ccf6145e7b45fec396541f801
Source dataset
uspto-grants-1998_09
Patent number
US05808071

Reaction notes

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