Allyl bromide → 1-(Prop-2-en-1-yl)-1,4-diazepane

To a solution of tert-butyl 1-homopiperazinecarboxylate (9.73 mL, 50 mmol) in dichloromethane (250 mL) was added PS-TBD resin (40 g, 100 mmol) and 3-bromoprop-1-ene (4.33 mL, 50 mmol) dropwise at 25° C. The mixture was stirred for 2 h. The PS-TBD was filtered off and the filtrate evaporated to dryness, redissolved in MeOH/EtOAc (1:9) and then filtered through a short silica column. The filtrate obtained was evaporated to dryness, treated with TFA (20 ml) and then stirred at room temperature for 1 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (50 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford 1-prop-2-enyl-1,4-diazepane (4.07 g, 58.0%) as a pale yellow oil.

1. filtrationThe PS-TBD was filtered off
2. customthe filtrate evaporated to dryness
3. dissolutionredissolved in MeOH/EtOAc (1:9)
4. filtrationfiltered through a short silica column
5. customThe filtrate obtained
6. customwas evaporated to dryness
7. additiontreated with TFA (20 ml)
8. stirringstirred at room temperature for 1 h
9. customThe reaction mixture was evaporated to dryness
10. dissolutionredissolved in MeOH (50 mL)
11. customthe crude product was purified by ion exchange chromatography
12. washThe desired product was eluted from the column
13. customevaporated to dryness

ORDレコード

ord-23a00e13c4e54f1cae11c9cd7c3712f0

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08129391B2