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Short Note

tert-Butyl methoxy(2-propynyl)carbamate

by
Vittorio E. Caprio
,
Michael W. Jones
and
Margaret A. Brimble
*
Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(3), M200; https://doi.org/10.3390/M200
Submission received: 8 December 2000 / Accepted: 15 December 2000 / Published: 25 March 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 06 m200 i001
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.

Supplementary Materials

Reference

  1. Brimble, M.A.; Duncalf, L.J. Molecules 2000, 5, 162–166. [CrossRef]
  2. Moore, D.H.; Cannon, J.G.; McIsaac, W.M.; Ho, B.T. J. Med. Chem. 1969, 12, 45–48. [CrossRef] [PubMed]
Sample availability: available from the authors.

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MDPI and ACS Style

Caprio, V.E.; Jones, M.W.; Brimble, M.A. tert-Butyl methoxy(2-propynyl)carbamate. Molecules 2001, 6, M200. https://doi.org/10.3390/M200

AMA Style

Caprio VE, Jones MW, Brimble MA. tert-Butyl methoxy(2-propynyl)carbamate. Molecules. 2001; 6(3):M200. https://doi.org/10.3390/M200

Chicago/Turabian Style

Caprio, Vittorio E., Michael W. Jones, and Margaret A. Brimble. 2001. "tert-Butyl methoxy(2-propynyl)carbamate" Molecules 6, no. 3: M200. https://doi.org/10.3390/M200

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