HCID 67270141, compound → HCID 67269606, compound

HRID 1039668Notes

Reaction equation

HRID 1039668 reaction equation
[C:1]([O:5][C:6](/[C:8](=[CH:13]\[C:14]1[CH:22]=[C:21]([F:23])[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)/[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][C:14]1[CH:22]=[C:21]([F:23])[C:17]2[O:18][CH2:19][O:20][C:16]=2[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 67270141HCID 67270141, compound

Product 1

HCID 67269606HCID 67269606, compoundYield 149.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of (Z)-methyl 2-(tert-butoxycarbonyl)-3-(7-fluorobenzo[d][1,3]dioxol-5-yl)acrylate (8000 mg) in 70 mL of methanol was added [(1S,1S′,2R,2R′) [Rh(duanphos)cod]BF4 (41.64 mg, 58.94 μmol; Strem). The mixture was purged with hydrogen 5 times and then sealed at 50 psi of H2 and stirred for 8 hours. Concentration and purification of the reaction crude by silica gel chromatography provided (S)-methyl 2-(tert-butoxycarbonyl)-3-(7-fluorobenzo[d][1,3]dioxol-5-yl)propanoate (12.0 g, 99.4%) as a colorless oil.

Workup

  1. customThe mixture was purged with hydrogen 5 times
  2. customsealed at 50 psi of H2
  3. concentrationConcentration and purification of the reaction crude by silica gel chromatography

Sources & evidence

ORD record
ord-4343063ba79645568e56d8e81a6634a1
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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