A facile method for the preparation of MOM-protected carbamates

Organic Letters

Volumn 11, Issue 2, 2009, Pages 273-275

  Barnes, David M ^a   Barkalow, Jufang ^a   Plata, Daniel J ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; METHYL CHLORIDE;

ARTICLE; CHEMISTRY; METHYLATION; PH; SYNTHESIS;

CARBAMATES; HYDROGEN-ION CONCENTRATION; METHYL CHLORIDE; METHYLATION;

EID: 61449265151     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8022769     Document Type: Article

References (25)

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11. (e) See also Kawabata et al. (Kawabata, T.; Ozturk, O.; Suzuki, H.; Fuji, K. Synthesis 2005, 505-508), where the MOM-group takes part in a Pictet-Spengler cyclization following its use in the memory of chirality alkylation.
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15. 4 has little effect on the outcome of the reaction. We observed differences in reaction rates when reactions in toluene were stirred magnetically or mechanically; these differences were not seen when the reaction was run in dichloromethane.
16. 4, and concentrated. Purification by column chromatography afforded 1.03 g (88% yield) of benzyl N-methoxymethyl(phenethyl)carbamate 5a.
17. These reactions were not further optimized.
18. 2 on carbamate 4a supported the N-chloromethyl structure shown in Scheme 1 relative to that of the imminium ion. See the Supporting Information.
19. This transformation has previously been accomplished in two steps in 14% overall yield. Kim, H. J.; Yoon, U. C.; Jung, Y.-S.; Park, N. S.;Cederstrom, E. M.; Mariano, P. S. J. Org. Chem. 1998, 63, 860-863.
20. 3): (a) Madin, A.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. Angew. Chem., Int. Ed. 1999, 38, 2934-2936 (cone. HCl).
21. (b) Yokoshima, S.; Tokuyama, H.; Fukuyama, T. Angew. Chem., Int. Ed. 2000, 39, 4073-4075 (TMS-Cl, NaI).
22. 3).
23. (d) Baran, P. S.; Guerrero, C. A.; Hafensteiner, B. D.; Ambhaikar, N. B. Angew. Chem., Int. Ed. 2005, 44, 3892-3895 (bromocatecholborane).
24. For the reaction of toluene sulfinic acid with formaldehyde, see: Brederek, H.; Bader, E. Chem. Ber. 1954, 87, 129-139.
25. Although the conditions described in this paper do not employ MOM-Cl as a reagent, it is possible that upon MeOH quench some MOM-Cl is in fact generated from the activated formaldehyde.