Water → Methyl 3alpha,7alpha-ditetrahydropyranyloxy-5beta-cholan-24-oate
Reaction equation
[C:1]1(C)C=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.[OH:18][C@@H:19]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@H:21]([CH2:22][C@@H:23]([OH:46])[C@@H:24]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C@H:29]([CH3:36])[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:20]1.[OH2:47]>O1CCOCC1>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:18][C@@H:19]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@H:21]([CH2:22][C@@H:23]([O:46][CH:5]3[CH2:4][CH2:3][CH2:2][CH2:1][O:47]3)[C@@H:24]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:25]3[CH2:26][CH2:27][C@@H:28]2[C@H:29]([CH3:36])[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH2:20]1Participants
6
Procedure
p-Toluenesulfonic acid (78 mg, 0.41 mmol), 3,4-dihydro-2H-pyrane (20.1 ml, 0.098 mol) were added to a solution of methyl 3α,7α-dihydroxy-5β-cholan-24-oate (1) (2.0 g, 4.9 mmol) in dioxane (6 mL). The reaction mixture was stirred at room temperature for 15 min. H2O (50 mL) was then added and the mixture was partially concentrated under vacuum and extracted with EtOAc (3×50 mL). The combined organic fractions were washed with brine (1×50 mL), dried (Na2SO4) and evaporated under vacuum. The residue was purified by chromatography on silica gel column. Elution with light petroleum/ethyl acetate 80/20 afforded 2.5 g of the pure compound 2 (90% yield).
Workup
- concentrationthe mixture was partially concentrated under vacuum
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic fractions were washed with brine (1×50 mL)
- dry with materialdried (Na2SO4)
- customevaporated under vacuum
- customThe residue was purified by chromatography on silica gel column
- washElution with light petroleum/ethyl acetate 80/20
Sources & evidence
- ORD record
- ord-e984c97df48947a3b63eb7d7b801d606
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410083B2
Reaction notes
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