3-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidine-1-carboxylic Acid Benzyl Ester → 4-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-ol
Reaction equation
C(OC([N:11]1[CH2:15][CH:14]([OH:16])[CH:13]([CH:17]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:18][CH:19]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[CH2:12]1)=O)C1C=CC=CC=1>CO>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH:19]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[O:18][CH:17]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:13]2[CH2:12][NH:11][CH2:15][CH:14]2[OH:16])=[CH:25][CH:24]=1Participants
3
Procedure
Compound 75 (8.25 g, 14.9 mmol) was dissolved in methanol (20 mL) and purged with argon. To the solution was added 10% palladium on carbon (0.825 g). The flask was purged with hydrogen 2 times and stirred further at room temperature under hydrogen atmosphere for 3 h. The disappearance of the starting material was confirmed by the TLC. The reaction mixture was filtered through a pad of Celite and washed with methanol. The combined organic layer was concentrated under reduced pressure to afford amine 76 (6.12 g, 98%) as white solid. This was used as such for the next step.
Workup
- custompurged with argon
- additionTo the solution was added 10% palladium on carbon (0.825 g)
- customThe flask was purged with hydrogen 2 times
- filtrationThe reaction mixture was filtered through a pad of Celite
- washwashed with methanol
- concentrationThe combined organic layer was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d6f0973ee99c481db33cdbf78f0d4665
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745608B2
Reaction notes
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