Reaktion #1726695

ord-701d5c5f91014782a137a564f32574f8

Reaktionsgleichung

Oc1ccc(CN2CC3(COC3)C2)cc1Cl
8A
Oc1ccc(CN2CC3(COC3)C2)cc1Cl
4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenol
Cc1ccc(S(=O)(=O)OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)cc1
8B
Cc1ccc(S(=O)(=O)OC2CN(C(=O)c3nnc(-c4ccccc4)o3)C2)cc1
1-(5-Phenyl-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl 4-methylbenzenesulfonate
O=C(c1nnc(-c2ccccc2)o1)N1CC(Oc2ccc(CN3CC4(COC4)C3)cc2Cl)C1
8
Ausbeute 51.6%
O=C(c1nnc(-c2ccccc2)o1)N1CC(Oc2ccc(CN3CC4(COC4)C3)cc2Cl)C1
(3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone
Ausbeute 51.6%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using a similar protocol as described in Example 2 but employing 8A (130 mg, 0.54 mmol) and 8B (220 mg, 0.55 mmol) as starting materials afforded 130 mg (51%) of 8 as a gum. 1H NMR (500 MHz, CD3OD): δ 3.38 (s, 4H), 3.48 (s, 2H), 4.25 (dd, 1H), 4.6-4.8 (m, 6H), 5.15 (m, 2H), 6.78 (d, 1H), 7.15 (d, 1H), 7.32 (s, 1H), 7.56 (t, 2H), 7.61 (t, 1H), 8.09 (d, 2H), MS (APCI+) m/z 467 [M+H]+, LC purity: 91%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08110566B2uspto-grants-2012_02