User:Aschwole/sandbox

1. The enantioselective synthesis starts with acylation of the chiral auxiliary derived from S-phenylalaninol

U.S. patent 4,816,470 (1989).

U.S. patent 5,037,845 (1991).

WO 0134561 

DOI: 10.3987/COM-97-8087 (one-pot)

DOI: 10.3987/COM-99-8815

Drugs of the Future, 1989,14, 35-39.

Activity at monoamine transporters (nM)

Compound	Mazindol	DA	5-HT	NE
cocaine	375	423	155	83.3
(–)-40	54.3	60.3	1.76	5.24
(+)-40	79	114	1.48	4.62
(±)40	61.7	60.3	2.32	2.69
29β	620	1420	8030
30β	186	492	97.7
31β	47.0	211	28.5
29α	4140	20100	3920
30α	3960	8850	696	1150
45	6.86	24.0	1.77	1.06
42a	4.00	2.23	14.0	2.99
41a	17.2	10.2	78.9	15.0
42b	3.61	11.3	25.7	4.43
50a	149	149	810	51.7
49a	13.7	14.2	618	3.84
(–)-4	10500	16500	1890	70900
(+)-4	18500	27600	4630	38300
(–)-5	9740	9050	11900	4650
(+)-5	6770	10500	25100	4530

Aschwole/sandbox

Identifiers
IUPAC name 1-Cyano-3-(4-cyanophenyl)-2-[(2R)-3,3-dimethyl-2-butanyl]guanidine
CAS Number	220641-11-2
PubChem CID	158438
ChemSpider	139379
Chemical and physical data
Formula	C15H19N5
Molar mass	269.345 g/mol g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@H](C(C)(C)C)/N=C(\NC#N)/NC1=CC=C(C=C1)C#N
InChI InChI=InChI=1S/C15H19N5/c1-11(15(2,3)4)19-14(18-10-17)20-13-7-5-12(9-16)6-8-13/h5-8,11H,1-4H3,(H2,18,19,20)/t11-/m1/s1 Key:PGYDRGZVXVVZQC-LLVKDONJSA-N