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Methanesulfonylation of phthalic anhydride protected phenylglycinol; (R)-2-(1,3-dioxoisoindolin-2-yl)-2-phenylethyl methanesulfonate

SyntheticPage 610
DOI: 10.1039/SP610
Submitted Jul 10, 2013, published Jul 12, 2013
Nikola P. Chmel (N.Chmel@warwick.ac.uk), Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: <IMG src="/images/empty.gif">Methanesulfonylation of phthalic anhydride protected phenylglycinol<IMG src="/images/empty.gif">

Chemicals Used

Methanesulfonyl chloride (Fluka)
Triethylamine (BDH)
(R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (Prepared in house, see page 609)

Procedure

Methanesulfonyl chloride (0.32 ml, 4.12 mmol) and TEA (0.57 ml, 4.12 mmol) were added to a solution of (R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.0 g, 3.7 mmol) in DCM (20 ml) and were stirred overnight. The resulting solution was washed with water (3 × 20 ml) and dried over anhydrous sodium sulphate. The solvents were removed under reduced pressure and the residue was used in the subsequent reaction without further purification. Yield 1.22 g (94%).

Author's Comments

Worked smoothly. Very reproducible.

Data

1H NMR (400 MHz, 298 K, CDCl3) δH 7. 84 (2H, dd, 3JHH = 5.4 Hz JHH = 3.1 Hz, Pht), 7.72 (2H, dd, 3JHH = 5.5 Hz, 3JHH = 3.0 Hz, Pht), 7.55 – 7.48 (2H, m, Ph), 7.40 – 7.31 (3H, m, Ph), 5.68 (1H, dd, 3JHH = 10.5 Hz 2JHH = 5.4 Hz, CH), 5.41 (1H, t, 3JHH = 10.4 Hz, CH2), 4.78 (1H, dd, 3JHH = 10.4 Hz, 2JHH = 5.4 Hz, CH2), 2.98 (3H, s, SO3CH3).

13C NMR (100 MHz, 298 K, CDCl3) δC 168.22 (C=O), 135.19, 134.44 (Pht), 131.77, 129.19, 128.20 (Ph), 123.66 (Pht), 67.23 (CH2), 54.25 (CH), 37.67 (SO3CH3).

MS (ESI+) m/z 368.0 ([M+Na]+), 250.1 ([M-SO3CH3]+)

IR (cm-1) ν 1774, 1708, 1611, 1544, 1496, 1468, 1386, 1355, 1335, 1290, 1266, 1205, 1174, 1136, 1110, 1087, 987, 961, 918, 902, 878, 809, 767, 720, 698

Lead Reference

D. B. Damon, R. W. Dugger, S. E. Hubbs, J. M. Scott and R. W. Scott, Organic Process Research & Development, 2006, 10, 472-480. http://dx.doi.org/10.1021/op060013i

Supplementary Information

1H NMR.jcamp

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Keywords: amines, aromatics/arenes, methanesulfonylation, phthalic anhydride, protection

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