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. Author manuscript; available in PMC: 2010 Apr 2.

Published in final edited form as: Org Lett. 2009 Apr 2;11(7):1499–1502. doi: 10.1021/ol900098q

Table 2.

Aminolysis of unactivated esters



entry	ester	amine	Temp °C	% yield^a
1	MeCO₂Me	PhCH₂NH₂	23	83 (3)
1	MeCO₂Me	PhCH₂NH₂	45	94 (4)
2	PhCO₂Me	PhCH₂NH₂	23	26^b (2)
2	PhCO₂Me	PhCH₂NH₂	70	92 (3)
3	Me(CH₂)₆CO₂Me	PhCH₂NH₂	23	43^b (1)
3	Me(CH₂)₆CO₂Me	PhCH₂NH₂	70	94 (2)
4	i-PrCO₂Me	PhCH₂NH₂	23	23^b (nd)
4	i-PrCO₂Me	PhCH₂NH₂	70	62 (2)
5	MeCH(OH)CO₂Me	PhCH₂NH₂	23^c	52^b (8)
5	MeCH(OH)CO₂Me	PhCH₂NH₂	23	84 (50)
6	MeCO₂Et	PhCH₂NH₂	23	58 ^b (1)
6	MeCO₂Et	PhCH₂NH₂	70	91 (7)
7	γ−butyrolactone	PhCH₂NH₂	23^c	84 (5)
8	Me(CH₂)₆CO₂Me	piperidine	23	2^b (nd)
8	Me(CH₂)₆CO₂Me	piperidine	95	77 (2)
9	Me(CH₂)₆CO₂Me	PhCH(Me)NH₂	23	1 ^b (nd)
9	Me(CH₂)₆CO₂Me	PhCH(Me)NH₂	95	71 (5)
10	Me(CH₂)₆CO₂Me	c-C₆H₁₁NH₂	23	3^b (nd)
10	Me(CH₂)₆CO₂Me	c-C₆H₁₁NH₂	95	84 (2)
11	(L)-Phe-OMe		90	79 (7)

^a

Isolated yield is given, unless specified otherwise. % Conversion by ¹H NMR in the absence of 18 is given in parentheses.

^b

Yield estimated by ₁H NMR

^c

Carried out in CDCl₃ at 1.0 M of amine