Methanol → (R)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)propanoate

HRID 532726Notes

Reaction equation

HRID 532726 reaction equation
[C:1]([O:5][C:6](/[C:8](=[CH:13]\[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([F:21])[CH:15]=1)/[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>CCOC(C)=O>[C:1]([O:5][C:6]([C@H:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([F:21])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 66617950(Z)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)acrylate

Product 1

HCID 66618233(R)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)propanoateYield 755.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(Z)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)acrylate (200 mg) and ca. Rh—(R,R)-[Et-DuPhos(COD)]OTf (4 mg) in 1:1 MeOH:EtOAc (3 mL; degassed 1 h with N2 prior to use) was dissolved in 8 Argonaut Endeavor™ reaction tubes. The reaction mixtures were put on the Endeavor™ under 40 psi H2 and stirred for 12 hours at room temperature. All of the reaction mixtures were then combined and concentrated to give (R)-methyl 2-(tert-butoxycarbonyl)-3-(4-chloro-3-fluorophenyl)propanoate (1.52 g, 94.4% yield) as a pale yellow solid, which was used without further purification in next step.

Workup

  1. customdegassed 1 h with N2
  2. dissolutionwas dissolved in 8 Argonaut Endeavor™ reaction tubes
  3. customThe reaction mixtures
  4. customAll of the reaction mixtures
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d04eaae38ec4a39a32cd1545c097551
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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