[7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester → (+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester

HRID 985785Notes

Reaction equation

HRID 985785 reaction equation
[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[S:6][C:7]2[C:13]([C:14]3[O:15][CH2:16][CH2:17][O:18][CH:19]=3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1.[H][H]>O1CCOCC1.C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[S:6][C:7]2[C:13]([CH:14]3[CH2:19][O:18][CH2:17][CH2:16][O:15]3)=[CH:12][CH:11]=[C:10]([O:20][CH3:21])[C:8]=2[N:9]=1

Participants

6

Reactant 2

HCID 60117387[7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 60117386(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl esterYield 79.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4.90 g (15.2 mmol) [7-(5,6-dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid methyl ester in 250 ml dioxane and 5 ml acetic acid was added 4.9 g of 10% palladium on charcoal and the mixture was then stirred for 24 h at room temperature under a 10 bar atmosphere of hydrogen. The mixture was then filtered, washing with dioxane, and the filtrate concentrated in vacuo. Trituration in acetone afforded 3.90 g (79%) (±)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid methyl ester as a white solid. ES-MS m/e (%): 325 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashing with dioxane
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e210795b9a0b4134b96e75487a5d0dab
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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