Diisobutylaluminumhydride → (2S, 4S)-1-N-Dodecy-4-(4-iodophenoxy)pyrrolidine-2-methanol
Reaction equation
[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][CH:20]=2)[CH2:15][C@H:14]1[C:26](OC)=[O:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:20]=[CH:21][C:22]([I:25])=[CH:23][CH:24]=2)[CH2:15][C@H:14]1[CH2:26][OH:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2S, 4S)-1-N-dodecyl-4-(4-iodophenoxy)pyrrolidine-2-carboxylic acid, methyl ester (2.09 g, 4.06 mmol) in tetrahydrofuran (20 ml) at −78° C. was added dropwise diisobutylaluminum hydride (1.0M in hexane, 15.0 ml, 15.0 mmol). After stirring at this temperature for 5 min. and at 0° C. for 2.5 h, the reaction was quenched with water at 0° C. After stirring at r.t. for 10 min., the mixture was diluted with ethyl acetate (250 ml), washed with 2N sodium hydroxide (3×100 ml), 35% sodium and potassium tartrate (2×100 ml), brine (100 ml), dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/ethyl acetate 3:1 to 2:1) to afford the title compound (1.65 g, 79%) as a colorless oil. [a]D=−18.5° (c 0.92, CHCl3).
Workup
- customthe reaction was quenched with water at 0° C
- stirringAfter stirring at r.t. for 10 min.
- additionthe mixture was diluted with ethyl acetate (250 ml)
- washwashed with 2N sodium hydroxide (3×100 ml), 35% sodium and potassium tartrate (2×100 ml), brine (100 ml)
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel (hexane/ethyl acetate 3:1 to 2:1)
Sources & evidence
- ORD record
- ord-c6dc61fa671c47399ac397d50c0da709
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350892B1
Reaction notes
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