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BOC protection and methylsulfonylation of phenylglycinol; (R)-2-(tert-butoxycarbonylamino)-2-phenylethyl methanesulfonate

SyntheticPage 607
DOI: 10.1039/SP607
Submitted Jul 09, 2013, published Jul 11, 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"><IMG src="/images/empty.gif">BOC protection and methylsulfonylation of phenylglycinol<IMG src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

BOC anhydride (Fluka)
(R)-phenylglycinol(Prepared in house, see Page 275)
TMEDA
Methanesulfonyl chloride (Fluka)

Procedure

BOC anhydride (1.68 g, 7.7 mmol) in THF (5 ml) was added dropwise to a solution of (R)-phenylglycinol Page 275 (1.0 g, 7.3 mmol) and was stirred for 30 min. TMEDA (0.90 g, 7.7 mmol) was added and the mixture was cooled in an ice/water bath. Methanesulfonyl chloride (0.89 g, 7.7 mmol) was added and the mixture was stirred for 1.5 h. The solids were removed by filtration and washed with THF. Hexanes were added to the combined filtrates to initiate the crystallisation. The product was collected by filtration, washed with hexanes and dried in air. Yield 2.0 g (87%).

Author's Comments

This was a reliable prep in our hands.

Data

1H NMR (400 MHz, 298 K, CDCl3) δH 7.42 – 7.28 (m, 5H, Ph), 5.25 – 5.09 (m, 1H, NH), 5.08 – 4.94 (m, 1H, CH), 4.55 – 4.33 (m, 2H, CH2), 2.88 (s, 3H, SO3CH3), 1.43 (s, 9H, tBu).

13C NMR (100 MHz, 298 K, CDCl3) δC 137.8, 129.09, 128.47, 126.82 (Ph), 71.38 (CH2), 53.7 (CH), 37.61 (SO3CH3), 28.44 (C(CH3)3)

MS (ESI+) m/z 338.0 ([M+Na]+)

IR (cm-1) ν 3357, 2982, 2939, 1693, 1522, 1497, 1456, 1391, 1356, 1329, 1277, 1252, 1163, 1099, 1079, 1053, 1028, 1002, 959, 923, 886, 851, 815, 758, 702, 653.


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

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Get structure file (.cdx, .sk2, .mol)

Keywords: addition, alcohols, amines, BOC, mesylate, methanesulfonylation, protecting group

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