2-(3-Methyl-2-pent-1-ynyl-benzoylamino)-indan-2-carboxylic acid ethyl ester → 2-[3-Methyl-2-((Z)-pent-1-enyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[C:24]#[C:25][CH2:26][CH2:27][CH3:28])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH3:28])[CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:14]1)=[O:5])[CH3:2]Participants
4
Procedure
To a solution of 2-(3-methyl-2-pent-1-ynyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (122) (300 mg, 0.77 mmol) in absolute EtOH (18 mL) is added the catalyst, Pd—C (50% wetted powder, 10% Pd, 30 mg, 1.4% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, room temperature, overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed by EtOH. The combined EtOH solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product as white solid (168 mg, 56%).
Workup
- customThe resulting reaction mixture
- custom50 psi, room temperature, overnight
- customThe catalyst is removed by the filtration through a pre-column (10 g silica gel)
- washwashed by EtOH
- concentrationThe combined EtOH solution is concentrated in vacuo
- customThe residue is purified by HPLC
Sources & evidence
- ORD record
- ord-461a4cda7ea04dd8a8189a8f3ccfe69e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569535B2
Reaction notes
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