Spectroscopy of N-methyllaurotetanine

Organic Chemistry II
SKO3033

NAME & MATRIX NUMBER 1. MUHAMAD AZIB BIN MD ALLADZHAR (D20162076205)

2. ABDUL RAHIM BIN MD SAAD (D20162075593)

LECTURER PROFESOR MADYA DR. MOHD AZLAN BIN NAFIAH

INTRODUCTION

The study is extracting, isolating and identifying alkaloids from

Alseodaphne corneri leaves. The isolation yields many alkaloids, but
the one that we are choosing is named N-methyllaurotetanine. The
structural elucitation of isolated alkaloid was carried out by
spectroscope techniquue, UV, IR, NMR and mass spectrometry
N-methyllaurotetanine structure
UV SPECTROSCOPY

- Used to determine the optical properties of substances

- Determine the substance concentration or the chemical
conversion of a substance in solution
- Useful in the structure elucidation of organic compound of organic
compound.
- Can know the compound is saturated or unsaturated
- The UV spectra shows absorption at 280 nm and 302 nm
UV SPECTROSCOPY
IR SPECTROSCOPY

- Deals with infrared region of the electromagnetic spectrum

- Divided into three region
- Near with higher energy IR, 14000𝑐𝑚−1 - 4000𝑐𝑚−1
- Mid infrared, 4000𝑐𝑚−1 - 400𝑐𝑚−1
- Far infrared, 400𝑐𝑚−1 - 10𝑐𝑚−1
IR SPECTRUM
MASS SPECTROSCOPY

- Mass spectrum exhibited a pseudomolecular ion peak, [M+H]+ at

m/z 342.2 with molecular formula C20H23NO4
MASS SPECTROSCOPY

[M+H]+
H-NMR SPECTROSCOPY
Position δH, ppm (J in Hz)

1 -
1a -
1b -
2 -
3 6.58 (s)
3a -
4 2.68 (d, 3.64)
3.16 (m)
5 2.51 (d, 3.64)
3.03 (dd, 5.96, 11.92)
6a 2.99 (m)
7 2.64 (d, 3.2)
2.95 (d, 4.12)
7a -
8 6.82 (s)
9 -
10 -
11 8.06 (s)

11a -

1-OMe 3.65 (s)

2-OMe 3.88 (s)
10-OMe 3.90 (s)
N-Me 2.54 (s)
H-NMR SPECTRUM

3.88
3.65

3.90 N-Me

4, 7

8.06
6.82
5,6a , 7
6.58
2.51
3.16
C-NMR SPECTROSCOPY
Position δc, (ppm)

1 144.22
1a 127.10
1b 127.20
2 152.00
3 110.31
3a 128.93
4 29.27
5 53.38
6a 62.63
7 34.32
7a 130.18
8 113.96
9 144.88
10 145.32
11 111.24
11a 124.04
1-OMe 60.24
2-OMe 55.85
10-OMe 56.13
N-Me 44.04
 C-NMR SPECTRUM

10-OMe
8 11
1-OMe
2-OMe
3
6a
5 7
10 9
2 3a 11a
4
1a 1b
1 N-Me
7a
DEPT SPECTRUM
10-OMe

1-OMe
2-OMe N-Me
11
6a
8
3

4
7
5
COSY SPECTRUM
H-6a H-7

H-7
H-6a
HMQC SPECTRUM
H Spectrum
H-7

C-7

C Spectrum
HMBC SPECTRUM
H Spectrum
H-7

C Spectrum
C-8
C-11a
C-1b
NOESY SPECTRUM
2-Ome & 10-OMe

6.58 H-3

8.06 C-11
3.88 & 3.90