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BOC protection of phenylglycinol; (R)-Tert-butyl 2-hydroxy-1-phenylethylcarbamate

SyntheticPage 611
DOI: 10.1039/SP611
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"><IMG alt="" src="/images/empty.gif">BOC protection of phenylglycinol<IMG alt="" src="/images/empty.gif"><IMG src="/images/empty.gif">

Chemicals Used

(R)-phenylglycinol (Prepared in house, see page 275)
THF (Fisher Scientific)
Triethylamine (BDH)
BOC anhydride (Fluka)

Procedure

(R)-phenylglycinol (1.0 g, 7.3 mmol) was dissolved in THF (10 ml) and cooled in an ice/water bath. A solution of di-tert-butyldicarbonate (1.08 g, 7.7 mmol) in THF (10 ml) and TEA (2.14 ml, 15.4 mmol) were added and the reaction mixture was stirred for 2 h at ambient temperature. The resulting solution was concentrated under reduced pressure to approximately half volume and hexanes were added to initialise crystallisation. The obtained solid was collected by suction filtration and washed with hexane. Yield 1.72 g (99%).

Author's Comments

Also reasonably insoluble in cold DCM

Data

1H NMR (400 MHz, 298 K, CDCl3) δH 7.36 – 7.21 (5H, m, Ph), 5.30 (1H, s br, NH), 4.74 (1H, s br, CH), 3.78 (2H, s br, CH2), 2.62 (1H, s, OH), 1.40 (9H, s, tBu).

13C NMR (100 MHz, 298 K, CDCl3) δC 156.29 (C=O), 139.65, 128.85, 127.79, 126.69 (Ph), 80.10 (C(CH3)3), 66.90 (CH2), 56.95 (CH), 28.46 (C(CH3)3).

MS (ESI+) m/z 260.1 ([M+Na]+)

IR (cm-1) ν 3237, 1670, 1605, 1584, 1547, 1493, 1469, 1454, 1431, 1392, 1367, 1343, 1314, 1283, 1255, 1232, 1159, 1103, 1054, 1027, 918, 866, 842, 760, 701, 663.


Lead Reference

M. Tiecco, L. Testaferri, F. Marini, S. Sternativo, C. Santi, L. Bagnoli and A. Temperini, Tetrahedron-Asymmetry, 2003, 14, 2651-2657.http://dx.doi.org/10.1016/S0957-4166(03)00498-1

Supplementary Information

1H NMR (1H NMR.jcamp)

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

Keywords: addition, alcohols, amines, aromatics/arenes, BOC protection, esters

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