methyl 7-[2-((Z)-3-{pyrrolidin-1-yl}prop-1-enyl)-4-fluorobenzene-sulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate → methyl cis-(3aRS,9bRS)-7-[2-(3-{pyrrolidin-1-yl}propyl)-4-fluorobenzenesulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate

HRID 927906Notes

Reaction equation

HRID 927906 reaction equation
[N:1]1([CH2:6]/[CH:7]=[CH:8]\[C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[S:16]([NH:19][C:20]2[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]3[C:23]([C:24]4[CH:36]=[CH:35][O:34][C:25]=4[CH2:26][O:27]3)=[CH:22][CH:21]=2)(=[O:18])=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>C(O)=O.[OH-].[OH-].[Pd+2]>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=2[S:16]([NH:19][C:20]2[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]3[C:23]([C@H:24]4[CH2:36][CH2:35][O:34][C@H:25]4[CH2:26][O:27]3)=[CH:22][CH:21]=2)(=[O:17])=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 66693484methyl 7-[2-((Z)-3-{pyrrolidin-1-yl}prop-1-enyl)-4-fluorobenzene-sulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86713241methyl cis-(3aRS,9bRS)-7-[2-(3-{pyrrolidin-1-yl}propyl)-4-fluorobenzenesulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylateYield 98.8%

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

A solution of methyl 7-[2-((Z)-3-{pyrrolidin-1-yl}prop-1-enyl)-4-fluorobenzene-sulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 15, 0.06 g) in IMS (4 mL) and formic acid (2 drops) was treated under an atmosphere of nitrogen with palladium hydroxide on carbon (10%, 0.02 g). The nitrogen was replaced by hydrogen and the mixture was stirred under an atmosphere of hydrogen for 1 hour. The mixture was filtered through Celite and the filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-7-[2-(3-{pyrrolidin-1-yl}propyl)-4-fluorobenzene-sulfonylamino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate (0.06 g) which was used without further characterisation.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-aeb42780671d453a9e5e61e461fb8a42
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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