Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → tert-Butyl 4-formylpiperidine-1-carboxylate

A solution of 1-(1,1-dimethylethyloxycarbonyl)-4-hydroxymethylpiperidine (20.7 g, 96.1 mmol) in dichloromethane (200 mL) was cooled to 0° C. and treated with pyridinium chlorochromate (31.1 g, 144.2 mmol). The suspension was allowed to warm to room temperature and stirred for 3 h. The mixture was then diluted with diethyl ether (250 mL), filtered through a pad of silica gel (50 mm×10 cm), and the solids washed with 4:1 hexane/acetone (3×250 mL). The filtrate was evaporated to leave a pale green oil. This oil was dissolved in ether (200 mL) and washed sequentially with 1N hydrochloric acid (2×100 mL), 1N aqueous sodium hydroxide (100 mL) and brine (100 mL). The aqueous washes were extracted with fresh diethyl ether (2×150 mL). The combined organic extract was dried over sodium sulfate, filtered and evaporated to afford the crude aldehyde (16.3 g, 76.42 mmol), which was used without purification.

1. filtrationfiltered through a pad of silica gel (50 mm×10 cm)
2. washthe solids washed with 4:1 hexane/acetone (3×250 mL)
3. customThe filtrate was evaporated
4. customto leave a pale green oil
5. washwashed sequentially with 1N hydrochloric acid (2×100 mL), 1N aqueous sodium hydroxide (100 mL) and brine (100 mL)
6. extractionThe aqueous washes were extracted with fresh diethyl ether (2×150 mL)
7. extractionThe combined organic extract
8. dry with materialwas dried over sodium sulfate
9. filtrationfiltered
10. customevaporated

ORD record

ord-86b59e5c988640e493036869a01a57b5

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719166