Methanol → HCID 54329089, compound
Reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8]([OH:12])([CH3:11])[CH2:7][N:6]1C(OC(C)(C)C)=O)=[O:4].CO.C(N(CC)CC)C.[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][C:8]([OH:12])([CH3:11])[CH2:7][N:6]1[S:43]([C:40]1[CH:39]=[CH:38][C:37]([O:36][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:42][CH:41]=1)(=[O:45])=[O:44])=[O:4]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 5-hydroxy-5-methyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.08 g) and 5 mL of methanol was added 10 drops of 12 M aqueous HCl. After stirring for 1 hour, the mixture was concentrated in vacuo, and the residue was dissolved in 1 mL of DMF. After cooling to 0° C., the mixture was treated with triethylamine (0.11 mL, 0.80 mmol) and 4-benzyloxy-benzenesulfonyl chloride (0.11 g, 0.40 mmol). After stirring for 2 h at room temperature, the mixture was diluted with ethyl acetate, washed 2× with 1M HCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by radial chromatography (2:1 hexane-ethyl acetate, 2 mm silica gel plate) affording 0.047 g of 1-(4-benzyloxy-benzenesulfonyl)-5-hydroxy-5-methyl-piperidine-2-carboxylic acid methyl ester as a colorless solid.
Workup
- concentrationthe mixture was concentrated in vacuo
- dissolutionthe residue was dissolved in 1 mL of DMF
- stirringAfter stirring for 2 h at room temperature
- washwashed 2× with 1M HCl
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by radial chromatography (2:1 hexane-ethyl acetate, 2 mm silica gel plate)
Sources & evidence
- ORD record
- ord-1904ce9c879f4b16ab5e251d629a31b0
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06329397B1
Reaction notes
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