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

HRID 985801Notes

Reaction equation

HRID 985801 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[O:16][CH2:17][CH2:18][O:19][CH:20]=3)=[CH:13][CH:12]=[C:11]([O:21][CH3:22])[C:9]=2[N:10]=1)[CH3:2].[H][H]>O1CCOCC1.C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[NH:5][C:6]1[S:7][C:8]2[C:14]([CH:15]3[CH2:20][O:19][CH2:18][CH2:17][O:16]3)=[CH:13][CH:12]=[C:11]([O:21][CH3:22])[C:9]=2[N:10]=1)[CH3:2]

Participants

6

Reactant 2

HCID 86594649[7-(5,6-Dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86594650(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid ethyl esterYield 62.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 12.0 g (35.7 mmol) [7-(5,6-dihydro-[1,4]dioxin-2-yl)-4-methoxy-benzothiazol-2-yl]-carbamic acid ethyl ester in 600 ml dioxane and 12 ml acetic acid was added 12 g of 10% palladium on charcoal and the mixture was then stirred for 48 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. Flash chromatography (1/1 acetone/dichloromethane) followed by trituration in ether and hexane afforded 7.50 g (62%) (±)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid ethyl ester as a white solid. ES-MS m/e (%): 339 (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-b1553d3a7e5444349e884241f3658024
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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