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Next: 2.2 Synthesis of the methylsilatrane: (1R,2S)-1',6,6-trimethyl-spirobicyclo3.1.1heptane-2,3'-5-aza-2,8,9-trioxa-1-silabicyclo3.3.3undecane Up: 2. Experimental Previous: 2. Experimental

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

 


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Next: 2.2 Synthesis of the methylsilatrane: (1R,2S)-1',6,6-trimethyl-spirobicyclo3.1.1heptane-2,3'-5-aza-2,8,9-trioxa-1-silabicyclo3.3.3undecane Up: 2. Experimental Previous: 2. Experimental
Bjoern Pedersen
1998-06-22