tert-Butyl Crotonate → (3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)pentanoate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	tert-Butyl Crotonate	HCID 5463127	—
Edukt	(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)-3-phenylpropionate	HCID 15344490	—
Edukt	tert-Butyl 4-methylpent-2-enoate	HCID 53938938	—
Edukt	(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-5-phenyl-4-pentenoate	HCID 86755224	—
Edukt	(3R,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-4-hexenoate	HCID 86755229	—
Lösungsmittel	Chloroform	HCID 6212	—
Produkt	(3S,alphaS)-t-Butyl 3-(alpha-methylbenzylamino)pentanoate	HCID 86755228	—

Reaktionsschritte

The title compound (31) was prepared from compound (10) of Example 3 using the above-described procedure. [α]D21 -54.0 (c 1.81, CHCl3); νmax (CHCl3)/cm-1 1724 s (C=O); δH (300 MHz; CDCl3) 7.36-7.20 (5H, m, Ph), 3.91 (1H, q, J=6.5, PhCHCH3), 2.68 (1H, m, NCHCH2), 2.39, 2.28 (2H, ABX system, JAB =14.3, JAX =5.7, JBX =5.5, CH2CO), 1.47 (9H, s, (CH3)3C), 1.41 (2H, m, CH3CH2), 1.34 (3H, d, J=6.5, PhCHCH3), 0.85 (3H, t, J=7.3, CH3CH2); δC (50 MHz; CDCl3) 172.19 (C=O), 146.44, (Ph:Cipso), 128.53, 126.92 (Ph:Cortho, Cmeta), 126.84 (Ph:Cpara), 80.23 (C(CH3)3), 55.01, 53.71 (CHN), 39.10 (CH2CO), 28.04 (C(CH3)3), 27.78 (CH3CH2), 24.80 (NCHCH3), 10.24 (CH3CH2); m/z (CI) 278 (MH+, 100%), 248 (5), 222 (30), 192 (12), 162 (15), 105 (20); (Found: C, 73.84; H, 10.11; N, 4.93. C17H27NO2 requires C, 73.61; H, 9.81; N, 5.05%).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US06037498
Quelldatensatz	uspto-grants-2000_03
ORD ID	ord-bc1aabb183e74b0fa553309505b2eb52
Quellennotiz	uspto-grants-2000_03