2.1 Synthesis of the chiral triethanolamine: (1R,2S)-2-$\lbrack$N,N-bis(2-hydroxyethyl)-aminomethyl$\rbrack$-6,6-dimethyl-2-hydroxybicyclo$\lbrack$3.1.1$\rbrack$heptane

A mixture of diethanolamine (1.05g, 10mmol) and (1R,2S)-$\beta$-pinene epoxid [8] (1.52g, 10mmol) was stirred at 120$^{\circ}$C for 2 days. Volatile impurities were distilled off at 120$^{\circ}$C (6mm). The residual yellow oil was used without further purification.

Yield 95 %; HPLC-ESI: m/e 257 (M⁺); calculated for C₁₄H₂₇NO₃: 257.37.

 

 

Table 1: ¹H NMR (CDCl₃) for 2( for numbering see figure 3)

$\delta$ (ppm)	mult.	J (Hz)	Int.	assignment
0.95	s		3H	9 (anti to C-7)
1.25	s		3H	8 (syn to C-7)
1.51	d	9.15	1H	7 (anti to CMe2)
1.66	m		1H	6
1.78	m		1H	5
1.80	m		1H	6
1.89	m		1H	4
1.93	m		1H	5
2.16	m		1H	2
2.17	m		1H	7 (syn to CMe2)
2.54	d	14.0	1H	10
2.70	d	14.0	1H	10
2.64, 2.76	m, m		4H	12 and 14
3.58, 3.68	m, m		4H	11 and 13
3.60	s (br)		3H	OH

 

 

Table 2: ¹³C NMR (CDCl₃) for 2( for numbering see figure 3)

$\delta$ (ppm)	mult.	assignment
23.83	CH3	9
25.06	CH2	5
27.25	CH2	7
27.46	CH3	8
29.48	CH2	6
38.06	Cq	3
40.96	CH	4
50.30	CH	2
59.01	2 $\times$ CH2	12 and 14
60.05	2 $\times$ CH2	11 and 13
66.78	CH2	10
76.21	Cq	1