Dichloromethane → HCID 70655308, compound
Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]1[CH2:14][CH2:13][N:12](C2N=CC(C(O)(C(F)(F)F)C(F)(F)F)=CN=2)[C@@H:11]([CH2:31][N:32]2[CH:37]3[CH:38]([OH:40])[CH2:39][CH:33]2[CH2:34][O:35][CH2:36]3)[CH2:10]1)(=[O:8])=[O:7].C(N([CH2:46][CH3:47])CC)C.S1[CH:52]=[CH:51][CH:50]=[C:49]1S(Cl)(=O)=O.[CH2:57](Cl)Cl>>[CH2:57]([O:40][CH:38]1[CH2:39][CH:33]2[N:32]([CH2:31][C@H:11]3[CH2:10][N:9]([S:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)(=[O:7])=[O:8])[CH2:14][CH2:13][NH:12]3)[CH:37]1[CH2:36][O:35][CH2:34]2)[C:47]1[CH:46]=[CH:52][CH:51]=[CH:50][CH:49]=1Participants
5
Reactant 4
Product 1
Conditions
- Temperature
- 0 °C
Procedure
A 50-mL round-bottomed flask was cooled to 0° C. and charged with 6-(benzyloxy)-8-((R)-piperazin-2-ylmethyl)-3-oxa-8-azabicyclo[3.2.1]octane trihydrochloride (endo) (700 mg, 1.64 mmol, Example 79, Step 3), triethylamine (1.14 mL, 8.20 mmol) and CH2Cl2 (10 mL). This was followed by thiophene-2-sulfonyl chloride (300 mg, 1.64 mmol, Sigma-Aldrich, St. Louis, Mo.) as a solution in CH2Cl2 (5 mL). After 10 min, the reaction was concentrated onto silica gel and purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2) to give 6-(benzyloxy)-8-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-3-oxa-8-azabicyclo[3.2.1]octane (endo) (250 mg) as a mixture of two isomers.
Workup
- concentrationthe reaction was concentrated onto silica gel
- custompurified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2)
Sources & evidence
- ORD record
- ord-196c0f0dc3a44929baf8219fef98d0e6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431563B2
Reaction notes
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