Dimethyl Sulfoxide → 1-Boc-piperidine-3-carboxaldehyde
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][OH:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl.O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH:24]=[O:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Conditions
- Temperature
- -68 °C
Procedure
DMSO (0.18 mL, 2.6 mmol) in CH2Cl2 (5 mL) was added dropwise to a solution of oxalyl chloride (2M in CH2Cl2, 0.65 mL, 1.3 mmol) in CH2Cl2 (4 mL) at −78° C. The resulting mixture was stirred at −68° C. for 15 minutes. 3-Hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (Dean A. Wacker et al. Bioorganic & Medicinal Chemistry Letters 2002, 12, 1785-1789) (0.22 g, 1.0 mmol) in CH2Cl2 (4 mL) was added dropwise and after 15 min stirring at −78° C., Et3N (6 mL) was added. The resulting solution was stirred at ambient temperature for 16 h. Water was added and the mixture was extracted with diethyl ether, the organic layer was dried (Na2SO4) and concentrated to give the product as an yellow oil (0.20 g, 92% yield). This crude product was used in the next step without further purification.
Workup
- stirringstirring at −78° C.
- stirringThe resulting solution was stirred at ambient temperature for 16 h
- extractionthe mixture was extracted with diethyl ether
- dry with materialthe organic layer was dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5c06e1106b2f4d9e820ad4fe73bdedfa
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829707B2
Reaction notes
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