(S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetic acid → (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-ethylnaphthalen-2-yl)acetic acid
Reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH:20]=[CH2:21])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CCO.[Rh]>[C:1]([O:5][C@@H:6]([C:10]1[C:19]([CH2:20][CH3:21])=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:3])[CH3:4]Participants
4
Procedure
To a solution of (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-vinylnaphthalen-2-yl)acetic acid (4 mg, 0.010 mmol) in EtOH (1.5 mL) was added Rh/Al2O3 (cat. amount) and the resulting mixture stirred under hydrogen (1 atm, balloon) at room temperature for 2 h. The reaction mixture was filtered over Celite, concentrated in vacuo and the residue was purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to provide 0.8 mg of the desired product. 1H-NMR: 400 MHz, (CD3OD) δ: 7.81 (d, J=4.2 Hz, 1H), 7.77 (s, 1H), 7.58-7.53 (m, 3H), 7.44-7.41 (m, 1H), 7.33-7.20 (m, 3H), 5.20 (s, 1H), 3.14-3.08 (m, 1H), 2.93-2.87 (m, 1H), 1.34 (t, J=7.4 Hz, 3H), 0.98 (s, 9H). LCMS-ESI− (m/z): [M−H]− calcd for C24H24ClO3: 395.1. Found: 395.0.
Workup
- filtrationThe reaction mixture was filtered over Celite
- concentrationconcentrated in vacuo
- customthe residue was purified by reverse phase HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA)
Sources & evidence
- ORD record
- ord-503323711b144dd398c102e3b408494c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102614B2
Reaction notes
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