Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[CH3:13].C(N(CC)CC)C>C(Cl)Cl.O>[C:12]([C:14]1([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=[O:11])[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of oxalyl chloride (3.0 mL, 34 mmol) in methylene chloride (400 mL) at −70° C. was added DMSO (4.8 mL, 68 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-(1-hydroxyeth-1-yl)-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (6.6 g, 17 mmol) in methylene chloride (125 mL) was slowly added over 15 min. After 1 h, triethylamine (19 mL, 136 mmol) was added and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford the title product (4.5 g).
Workup
- waitAfter 1 h
- extractionextracted three times with methylene chloride
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography (10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-8f33fd77764b4fe7a6059f8325c13e1b
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091211B2
Linked notes
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