Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 56640794, compound
Reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33]([C@@H:35]2[CH2:40][CH2:39][C:38](=[N:41][O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:37][NH:36]2)=[O:34])[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([NH:32][C:33]([C@@H:35]2[CH2:40][CH2:39][C@@H:38]([NH:41][O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:37][NH:36]2)=[O:34])[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
(+)-Camphorsulfonic acid (0.350 g, 1.51 mmol) and tetrahydrofuran (1 ml) was added to 4-[({(2S)-5-[(benzyloxy)imino]piperidin-2-yl}carbonyl)amino]piperidine-1-carboxylic acid benzyl ester (0.113 g, 0.25 mmol), and the obtained mixture was cooled down to −20° C. Borane-tetrahydrofuran complex (0.95M, 1.3 ml, 1.24 mmol) was added to the mixture, and after 9 hours of stirring, saturated sodium hydrogen carbonate aqueous solution (5 ml) was added. The reaction mixture was extracted with ethyl acetate (10 ml), and the organic layer was dried with anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain the title compound (95.3 mg) as brown oil (crude yield: 84%). The diastereo selectivity was (2S,5R)/(2S,5S)=93.2/6.8 (86.4% de).
Workup
- additionBorane-tetrahydrofuran complex (0.95M, 1.3 ml, 1.24 mmol) was added to the mixture
- extractionThe reaction mixture was extracted with ethyl acetate (10 ml)
- dry with materialthe organic layer was dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-58f95710bbb1477aa78722a0a7c4a525
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096523B2
Reaction notes
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