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14th March 2012 @ 23:25
SM recovered.

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Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium triacetoxyborohydride in 1,2-DCE.

38-3.png

Reaction Start Time: Approx 10.45 15/03/12
Glycinamide hydrochloride (66 mg, 0.60 mmol, 1.3 equiv.) was stirred in 1,2-DCE (5 mL) with freshly activated mol. sieves. Triethylamine (82 μL, 0.60 mmol, 1.3 equiv.) was added and the reaction stirred for approx 5 minutes. Aldehyde PMY 2-5 (100 mg, 0.46 mmol, 1 equiv.) was added. After 30 minutes, sodium triacetoxyborohydride (195 mg, 0.92 mmol, 2.0 equiv.) was added. Reaction is a hazy suspension. Further 1,2-DCE (10 mL) was added. Still a hazy suspension. No reaction after approx. 23 hours by TLC. MgSO4 added and the reaction heated to reflux. 19/03/12 Reaction is a dark brown mixture, no change by TLC. Reaction was cooled and filtered through celite (DCM). 10% NaHCO3 (25 mL) was added to the filtrate and stirred for 10 minutes. The layers separated and the aqueous extracted with DCM (2 × 20 mL). The combined extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to a brown solid/gum (148 mg). 1H NMR shows mostly SM aldehyde.

TLC (10% MeOH/DCM) visualised with UV and vanillin:
Final TLC
TLC
TLC 5 hours


NMR:
1H NMR crude


See also:
Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium triacetoxyborohydride (PMY 38-2)

Risk and Hazard Assessment:
See: Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination (PMY 38-1)
Also 1,2-dichloroethane is irritant to eyes, skin and respitory system, highly flammable and may cause cancer.
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Attached Files
Scheme
1H NMR crude
TLC
TLC 5 hours
Final TLC