KlementineJBS
commented
10 months ago 13.11.23
- Added 1,6-diaminohexane (397 mg, 3.42 mmol, 0.6 equiv.) and NEt3 (1.2 mL, 8.57 mmol, 1.5 equiv.) to a flask with 20 mL DCM
- Added nosyl chloride (1.261 g, 5.71 mmol). Reaction bubbled up vigorously and some reaction mixture was lost. Reaction was a dark swamp green colour.
- Stirred for ~1 hr. TLC indicated completion.
- Quenched with 20 mL NH4Cl solution (sat.)
- Diluted with water (100 mL)
- Extracted with DCM (2 x 100 mL, 1 x 50 mL), washed with brine and dried over mag sulphate. Rotovapped down, transferred to a vial and left blowing down under nitrogen.
*Product is not very soluble in DCM - should try chloroform next time.
Link to HIRAC and master page.
KBS43 - Nosyl protection of linear diamine .docx
Rationale
Nosyl is an electron deficient PG and will help to stabilise the N- required during the alkylation reaction. Alternatiavely, a nosyl-protected amine could participate in the Fukuyama-Mitsunobu reaction.
Reaction scheme
Outcome
525.7 mg, 1.08 mmol, 32%