Aluminium lithium hydride → (S)-2-(N,N-Dibenzylamino)-1-pentanol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]([C@@H:22]([CH2:33][CH2:34][CH3:35])[C:23](OCC1C=CC=CC=1)=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:15]([N:14]([C@@H:22]([CH2:33][CH2:34][CH3:35])[CH2:23][OH:24])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cold (0° C.) suspension of LiAlH4 (184 mg, 4.84 mmol) in THF (10 mL), a solution of ester 9 (375 mg, 0.97 mmol) in THF (2.5 mL) was added. The mixture was stirred at 0° C. for 2 h, and then quenched by dropwise addition of EtOH (3 ml). Na—K tartrate solution (10% aq, 30 mL) was added, and the crude was extracted with EtOAc (3×30 mL), dried over Na2SO4, concentrated in vacuo and purified by column chromatography on silica (hexane/EtOAc 5:1) to obtain alcohol 10 as a colorless oil (170 mg, 62% yield).
Workup
- customquenched by dropwise addition of EtOH (3 ml)
- additionNa—K tartrate solution (10% aq, 30 mL) was added
- extractionthe crude was extracted with EtOAc (3×30 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- custompurified by column chromatography on silica (hexane/EtOAc 5:1)
Sources & evidence
- ORD record
- ord-b237fdfe99ca4bf49e605cd7b24785e6
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138547B2
Reaction notes
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