(R)-Solketal → (1R,2S)-4'-(4-chlorophenyl)-2-(methoxymethyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Participants

Role	Name	HCID	Charge
Reactant	(R)-Solketal	HCID 736056	—
Reactant	(2'R,9S)-7-(4-chlorophenyl)-2'-(methoxymethyl)-4,5,13-trimethylspiro[3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaene-9,1'-cyclopropane]	HCID 57345408	—
Product	(1R,2S)-4'-(4-chlorophenyl)-2-(methoxymethyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]	HCID 57404939	—

Reaction Steps

The above employed synthesis scheme was identical to that set forth for Compound 202, except that (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol was used as starting material and the indicated enantiomers were produced at each step. LRMS (M+H)+: 413 m/z. 1H NMR (two conformers detected in ˜1:1 ratio) (400 MHz, DMSO-d6) δ 7.38-7.56 (m, 4H), 3.82 (dd, J=7.32, 10.76 Hz, 0.5H), 3.71 (dd, J=6.87, 10.99 Hz, 0.5H), 3.39 (s, 1.5H), 3.21 (dd, J=6.41, 10.76 Hz, 0.5H), 3.04 (dd, J=7.44, 10.87 Hz, 0.5H), 2.96 (s, 1.5H), 2.60 (s, 3H), 2.39 (s, 1.5H), 2.38 (s, 1.5H), 2.16-2.26 (m, 0.5H), 2.05 (dd, J=5.26, 9.61 Hz, 0.5H), 1.58 (s, 1.5H), 1.54 (s, 1.5H), 1.43-1.52 (m, 0.5H), 1.33-1.39 (m, 0.5H), 1.03 (dd, J=5.26, 9.38 Hz, 0.5H), 0.60 (t, J=6.07 Hz, 0.5H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249161B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-dd5b79d0cab0455dba26f7f7d10a3a22
Source note	uspto-grants-2016_02