| Identification | Back Directory | [Name]
(S)-N,N-Dimethyl-N | [CAS]
114318-94-4 | [Synonyms]
(S)-N,N-Dimethyl-N
Methanimidamide, N'-[1-[(1,1-dimethylethoxy)methyl]-2-methylpropyl]-N,N-dimethyl-, (R)- (9CI) | [Molecular Formula]
C12H26N2O | [MDL Number]
MFCD17019306 | [MOL File]
114318-94-4.mol | [Molecular Weight]
214.35 |
| Chemical Properties | Back Directory | [alpha ]
[α]D -59.6° (c 3.5, EtOH) | [Boiling point ]
261.0±42.0 °C(Predicted) | [density ]
0.86±0.1 g/cm3(Predicted) | [pka]
10.79±0.50(Predicted) |
| Hazard Information | Back Directory | [Uses]
(S)-N,N-Dimethyl-N′-(1-t-butoxy-3-methyl-2-butyl)formamidine is used for chiral auxiliary for derivatization, directed lithiation, and asymmetric alkylation adjacent to nitrogen of benzylic
or allylic secondary amines by formamidine exchange, metalation, alkylation, and hydrolysis.[1,2] | [Preparation]
Preparative Methods of (S)-N,N-Dimethyl-N′-(1-t-butoxy-3-methyl-2-butyl)formamidine: easily prepared from (S)-valinol in a high yielding four-step procedure (eq 1).[2] Other
chiral formamidines can be prepared and used successfully in the methodology outlined here (eq 2).[2,3]
 | [storage]
(S)-N,N-Dimethyl-N′-(1-t-butoxy-3-methyl-2-butyl)formamidine stores under argon at rt; use in a fume hood.
| [References]
1. (a) Meyers, A. I. T 1992, 48, 2589. (b) Meyers, A. I.; Highsmith, T. K. In Advances in Heterocyclic Natural Product
Synthesis; Pearson, W. H., Ed.; JAI Press: Greenwich, CT, 1990. (c) Meyers, A. I. Aldrichim. Acta 1985, 18, 59. (d)
Meyers, A. I. H 1984, 21, 360.
2. (a) Dickman, D. A.; Boes, M.; Meyers, A. I. OSC 1993, 8, 204. (b) Meyers, A. I.; Boes, M.; Dickman, D. A. OSC 1993,
8, 573.
3. (a) Meyers, A. I.; Hutchings, R. H. T 1993, 49, 1807. (b) Meyers, A. I.; Elworthy, T. R. JOC 1992, 57, 4732. |
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