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BOC protection of phenylglycinol

SyntheticPage 611

Submitted: July 10, 2013, published: July 12, 2013

Authors

Nikola P. Chmel (N.Chmel@warwick.ac.uk)

Pratik Gurnani (pratik.gurnani@warwick.ac.uk)

A contribution from 

Reaction Scheme

Chemicals

(R)-phenylglycinol (Prepared in house, see page 275)
THF (Fischer 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 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

Keywords

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