Hydrochloric Acid → N-Boc sphingosine
Reaction equation
[OH:1][CH2:2][C@H:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C@H:4]([OH:20])[C:5]#[C:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1COCC1>[C:24]([O:23][C:22]([NH:21][C@H:3]([C@@H:4](/[CH:5]=[CH:6]/[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[OH:20])[CH2:2][OH:1])=[O:28])([CH3:27])([CH3:26])[CH3:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 0.21 mmol) obtained in the above-described reaction was dissolved in THF (21 ml) and cooled to 0° C.; a 65% toluene solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) (258 μl, 0.850 mmol) was subsequently added dropwise. The resulting mixture was heated to room temperature and stirred for 2.5 hours. 1 M hydrochloric acid was subsequently added to the mixture, and the reaction was stopped; the mixture was extracted with diethylether, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to produce N-tert-butoxycarbonyl sphingosine (52 mg, 64%).
Workup
- temperatureThe resulting mixture was heated to room temperature
- extractionthe mixture was extracted with diethylether
- dry with materialthe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe concentrate was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f41fee3654bd496bb9223df415f5ee13
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093395B2
Reaction notes
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