m-Fluorobenzenethiol → HCID 59207197, compound

HRID 1013607Notes

Reaction equation

HRID 1013607 reaction equation
[NH:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.C1(P(C2C=CC=CC=2)[C:13]2[C:26]3O[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4P(C4C=CC=CC=4)C4C=CC=CC=4)[C:18]([CH3:41])(C)[C:17]=3C=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[F:57][C:58]1[CH:59]=[C:60]([SH:64])[CH:61]=[CH:62][CH:63]=1>O1CCOCC1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH4+:1].[OH-:5].[F:57][C:58]1[CH:59]=[C:60]([S:64][C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:41][N:1]2[CH2:4][CH:3]([OH:5])[CH2:2]2)[CH2:17][CH2:26][CH2:13]3)[CH:61]=[CH:62][CH:63]=1

Participants

9

Reactant 4

HCID 75710m-FluorobenzenethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 15142903-Hydroxyazetidine

Product 2

HCID 14923Ammonium HydroxideHCID 59207197HCID 59207197, compoundYield 465.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In 5 mL dioxane under argon was mixed 1-(R)-6-Iodo-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl)-azetidin-3-ol (0.172 g, 0.5 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.023 g, 0.025 mmoles), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.029 g, 0.05 mmol), diisopropylethyl amine (1 mmol) and 3-fluoro-thiophenol (0.13 g, 1.0 mmoles). The reaction mixture was stirred at 60° for 45 minutes, then was cooled and diluted with EtOAc. The organic layer was washed 1.5 M aqueous sodium carbonate, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue was subjected to preparative HPLC (hexanes/EtOAc 1:1 to 50% hexanes/27% EtOA/15% MeOH/8% con. NH4OH) to give 0.08 g (47%) of 1-[(R)-6-(3-fluoro-phenylsulfanyl)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-azetidin-3-ol, MS M+H=344.

Workup

  1. temperaturewas cooled
  2. washThe organic layer was washed 1.5 M aqueous sodium carbonate
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a2da11406f54aeba454317d1f7c9de6
Source dataset
uspto-grants-2011_07
Patent number
US07981923B2

Reaction notes

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