Methanol → HCID 86746411, compound

HRID 865409Notes

Reaction equation

HRID 865409 reaction equation
[C:1]([NH:4]/[C:5](=[CH:10]\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].[H][H].[CH3:19]O>[Rh]>[CH3:19][N:4]([C:1](=[O:3])[CH3:2])[C@@H:5]([C:6]([OH:8])=[O:7])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 996450652386-78-4HCID 178418361HCID 178418361, compound

Product 1

HCID 86746411HCID 86746411, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Conditions

Temperature
20 °C

Procedure

A 100 mL Fisher-Porter tube was charged with methyl (Z)-α-acetamidocinnamate (300 mg, 1.36 mmol), rhodium catalyst [(COD)Rh(1,2-Bis((2R,5R)-2,5-diethylphospholano)benzene)]+CF3SO3- prepared as in Example 15 (1.0 mg, 0.00136 mmol), MeOH (6.0 mL), and a stir bar. After sealing, the pressure head was then connected to a hydrogen tank (Matheson, 99.998%) and the lines were purged of air by four vacuum/H2 cycles. After two vacuum/H2 cycles on the reaction mixture, the tube was pressurized to an initial pressure of 30 psig H2. The reaction was allowed to stir at 20° C. for 2 h after which no further H2 uptake was observed. Complete conversion to product was indicated by capillary GC (methyl silicone column). The reaction was concentrated on a rotovap and the residue was chromatographed on a short SiO2 column (ca. 6×0.5 cm) using 80% ethyl acetate/hexane as eluent. The fractions containing product were concentrated on a rotovap to give methyl (R)-N-acetylphenylalanine as a colorless crystalline solid (270 mg, 90%). Enantiomeric excess analysis by HPLC using Daicel Chiralcel OJ column as described above indicated 99% enantiomeric purity. Other substrates were hydrogenated using the above procedure and the resulting data is summarized in Tables 1 and 2.

Workup

  1. customthe lines were purged of air by four vacuum/H2 cycles
  2. concentrationThe reaction was concentrated on a rotovap
  3. customthe residue was chromatographed on a short SiO2 column (ca. 6×0.5 cm)
  4. additionThe fractions containing product
  5. concentrationwere concentrated on a rotovap

Sources & evidence

ORD record
ord-17ff843776f3401a8a3650d381af641d
Source dataset
uspto-grants-1996_10
Patent number
US05565593

Reaction notes

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