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8th August 2013 @ 06:03
Aew: 60-80

Repeat of Reductive alkylation of glycinamide (PMY 51-2)


Glycinamide hydrochloride (2.00 g, 18.1 mmol, 1 equiv.) was dissolved in water (2 mL, heated then cooled). Sodium hydroxide (0.77 g, 19.3 mmol, 1.07 equiv) was added. The reaction was stirred for 20 mins but no precipitate formed (as previously described by PMY). Water removed under vacuum to give a white crystalline residue. The residue was stirred in methanol (45 mL) and acetic acid (4.5 mL) to give a hazy partial solution. Benzaldehyde (1.85 mL, 18.1 mmol, 1 equiv.) added and the mixture stirred at room temperature for 20 minutes. Sodium cyanoborohydride (1.25 g, 19.9 mmol, 1.1 equiv.) was added portionwise over 25 minutes and left to stir at room temperature overnight (5.40 pm).

Hazard and Risk Assessment:

See: Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride (PMY 38-4) Reaction scaled up from previous by factor of 4 (from 4.5 to 18.1 mmol), but has already been performed on this scale see: Reductive alkylation of glycinamide (PMY 51-2) .