Ammonia → 1,4-Dioxaspiro[4.5]decan-8-amine

Temperature

5 °C

Ammonia gas was bubbled into a solution of 1,4-dioxaspiro[4.5]decan-8-one (31.2 g, 199.77 mmol, 1.00 equiv) in methanol (300 mL). The resulting solution was stirred for 8 hrs at 0-10° C. This was followed by the addition of sodium borohydride (11.4 g, 301.35 mmol, 1.51 equiv) in several batches at 0-10° C. The resulting solution was stirred for 1 h at room temperature. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 4×300 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 20 g (64%) of 1,4-dioxaspiro[4.5]decan-8-amine as colorless oil.

1. stirringThe resulting solution was stirred for 1 h at room temperature
2. extractionThe resulting solution was extracted with 4×300 mL of dichloromethane
3. washThe resulting mixture was washed with 2×100 mL of brine
4. dry with materialThe mixture was dried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum

ORD record

ord-8601df8972924a6aae237b5c938b1235

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703941B2