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2nd October 2012 @ 02:49

PMY 2-5 (50 mg, 0.23 mmol, 1 equiv.) was dissolved in MeOH (2.0 mL) and acetic acid (0.06 mL) then 4-amino-1-benzylpiperidine (61 mg, 0.30 mmol, 1.3 equiv.) in MeOH (0.5 mL) was added. Reaction mixture stirred for 2 hours at room temperature and then sodium cyanoborohydride (16 mg, 0.25 mmol, 1.1 equiv.) added in two portions over 2 minutes. TLC after 4.5 hours showed SM still present. Reaction complete by TLC at 21 hours; 2(+) product spots. The mixture was concentrated under reduced pressure then treated with 1M NaOH (2.5 mL). The mixture was then extracted with DCM (3 x 5 mL). The extracts were washed with brine then dried (MgSO4) and concentrated to give an orange oil. Flash chromatography over silica (1 - 10% MeOH in DCM) gave the desired product as a pale yellow oil (19 mg, 0.05 mmol, 21 % yield).

TLC (25% EtOAc in hexane) after 4.5 hours (UV and vanillin):

AEW 9-2 van.jpg
AEW 9-2.jpg

TLC (5% MeOH in DCM) after 21 hours (UV and vanillin):

AEW 9-2 Vanillin 21 h.jpg
AEW 9-2 UV 21 hours.jpg

1HNMR 200 MHz:

AEW 9-2 purif.pdf

Crude:

AEW 9-2 crude.zip

Pure:

AEW 9-2 purif.zip

1HNMR 300 MHz:

AEW 9-2 purif.zip
AEW 9-2 frac 2.zip

See Also:Reductive Amination (AEW 9-1) Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (PMY 38-5) Reductive alkylation of glycinamide (PMY 51-2) Reductive amination of pyrrole aldehyde with crude PMY 53-2 (PMY 56-1) Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride (PMY 38-4)

Hazard and Risk Assesment:

AEW 9-2 HIRAC.pdf
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Attached Files
AEW 9-2.png
AEW 9-2 HIRAC.pdf
AEW 9-2.jpg
AEW 9-2.jpg
AEW 9-2 van.jpg
AEW 9-2 UV 21 hours.jpg
AEW 9-2 Vanillin 21 h.jpg
AEW 9-2 Vanillin 21 h.jpg
AEW 9-2.png
AEW 9-2 crude.zip
AEW 9-2 purif.zip
aew9-2prod.png
AEW 9-2 frac 2.zip
AEW 9-2 purif.pdf