tert-Butyl methoxy(2-propynyl)carbamate

Vittorio E. Caprio, Michael W. Jones and Margaret A. Brimble*

Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand, Fax: (+64 9) 3737599; E-mail: [email protected]

* Author to whom correspondence should be addressed.

Received: 8 December 2000 / Accepted: 15 December 2000 / Published: 25 March 2001

The general part of the experimental section [1] has been presented elsewhere. Di-tert-butyl dicarbonate (3.60 g, 13.2 mmol) and 4-(dimethylamino)pyridine (84 mg, 0.687 mmol) were added to a solution of amine 1 [2] (1.12 g, 13.2 mmol) in acetonitrile (14 mL) under nitrogen at room temperature and stirred for 21 h. The yellow liquid was concentrated under reduced pressure to generate a yellow oil that was purified by flash chromatography using hexane-diethyl ether (3:2) as eluent to afford the title compound 2 (1.77 g, 73%) as a colourless oil.

IR (neat): 3292m, 2980s, 2938m, 2125w, 1713s, 1370s, 1278s, 1243s, 1165s.

¹H NMR (200 MHz, CDCl₃): 1.48 [9H, s, OC(CH₃)₃], 2.24 (1H, t, J 2.4 Hz, CCH), 3.77 (3H, s, OCH₃), 4.19 (2H, d, J 2.4 Hz, NCH₂).

¹³C NMR (50 MHz, CDCl₃): 28.1 [CH₃, OC(CH₃)₃], 39.5 (CH₂, NCH₂), 63.0 (CH₃, OCH₃), 71.5 (CH, HCC), 71.8 (quat., CC), 81.6 [quat., OC(CH₃)₃], 156.2 (quat., N-C(=O)-O).

CI-MS: 186 (MH⁺, 18%), 158 (24%), 147 (90%), 130 (56%), 124 (9%), 105 (17%), 86 (100%).

Anal. Calc. For. C₉H₁₅NO₃(H+) 186.11302; found (MH)+, 186.11303.

Reference

1. Brimble, M. A.; Duncalf, L. J. Molecules 2000, 5, 162-166.
2. Moore, D.H.; Cannon, J.G.; McIsaac, W.M.; Ho, B. T. J. Med. Chem. 1969, 12, 45-48.

Sample availability: available from the authors.

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