Dimethyl Sulfoxide → tert-Butyl 4-formyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate

To a solution of oxalyl chloride (3.3 mL, 38 mmol) in methylene chloride (500 mL) at −70° C. was added DMSO (5.4 mL, 76 mmol) over 5 min. After 15 min, a solution of tert-butyl 4-hydroxymethyl-4-(2-(tert-butyldimethylsilyloxy)eth-1-yl)piperidine-1-carboxylate (7.1 g, 19 mmol) in methylene chloride (125 mL) was slowly added over 15 min. After 1 h, triethylamine (21.2 mL, 152 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 (40% ethyl acetate in hexanes) to afford the title product (6.3 g).

1. waitAfter 1 h
2. extractionextracted three times with methylene chloride
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography (40% ethyl acetate in hexanes)

ORDレコード

ord-4bd35abee2ce4dad988436debf719e15

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091211B2