Aluminium lithium hydride → HCID 71436860, compound

Temperature

10 °C

To a suspension of lithium aluminum hydride (2.8 equiv.) in dry THF (1.7 M) was added a solution of crude methyl 3-amino-2,2-dimethylcyclobutanecarboxylate (1.0 equiv.) in dry THF (0.7 M) at 0° C. Then the mixture was stirred under vigorously at 10° C. for 0.5 h, and then heated to 35-40° C. for 12 h. The reaction was quenched by addition of water, aqueous sodium hydroxide solution (3N) slowly at 0° C., and water. The mixture was stirred at 10° C. for 20 min, filtered through celite, and washed with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the crude title compound (3-amino-2,2-dimethylcyclobutyl)methanol as a racemic mixture (89.7% yield).

1. temperatureheated to 35-40° C. for 12 h
2. customThe reaction was quenched by addition of water, aqueous sodium hydroxide solution (3N) slowly at 0° C.
3. stirringThe mixture was stirred at 10° C. for 20 min
4. filtrationfiltered through celite
5. washwashed with ethyl acetate
6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-cf1e7cf9d87b4cec9d2bc58f45619772

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156798B2