Tetrahydrofuran → [(2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidin-2-yl]methanol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.C([O:14][C:15]([C@H:17]1[CH2:21][CH2:20][C@@H:19]([C:22]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[C:24]([F:30])[CH:23]=2)[NH:18]1)=O)C.[OH-].[Na+]>O>[F:28][C:26]1[CH:27]=[C:22]([C@H:19]2[NH:18][C@@H:17]([CH2:15][OH:14])[CH2:21][CH2:20]2)[CH:23]=[C:24]([F:30])[C:25]=1[F:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -15 °C
Procedure
LAH (483 mg) was added to a THF solution (50 mL) of (2R,5S)-5-(3,4,5-trifluorophenyl)pyrrolidine-2-carboxylic acid ethyl ester (2.91 g) over 1 hr at −15° C. The resulting reaction solution was stirred at −15° C. for 19 hr. To the reaction solution, water (0.5 mL), a 5 N sodium hydroxide aqueous solution (0.5 mL), and water (1.5 mL) were added in this order. The resulting mixture was stirred at room temperature for 30 min and then filtered through Celite. The filtrate was concentrated under reduced pressure to give 2.4 g of the title compound. The physical property values of this compound were as follows:
Workup
- customThe resulting reaction solution
- stirringThe resulting mixture was stirred at room temperature for 30 min
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-06216df421d042e5a78da4bf596942dd
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737141B2
Reaction notes
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