Triphenylphosphine → 1,1-Dimethylethyl 4-[(1-methyl-1H-tetrazol-5-yl)thio]-1-piperidinecarboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[SH:34][C:35]1[N:39]([CH3:40])[N:38]=[N:37][N:36]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:34][C:35]2[N:39]([CH3:40])[N:38]=[N:37][N:36]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-tert-butoxycarbonyl-4-hydroxypiperidine (1.01 g, 5.0 mmol) in dry THF (30 mL) were added triphenylphosphine (2.0 g, 7.5 mmol) and 5-mercapto-1-methyl-1H-tetrazole (0.70 g, 6.0 mmol). To the mixture was added diisopropyl azodicarboxylate (1.2 mL, 6.0 mmol) under ice cooling, and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (100 mL), which was washed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride, successively. The solvent was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (50 g, diethyl ether-hexane 1:1) to give the titled compound as a colorless oily substance. (1.11 g, 74%).
Workup
- washwas washed with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
- dry with materialThe solvent was dried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (50 g, diethyl ether-hexane 1:1)
Sources & evidence
- ORD record
- ord-84cb0a1613ba4a18b48b3ac6827a6216
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562978B1
Reaction notes
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