R-(-)-1,2-Propanediol → (1S,2R)-4'-(4-chlorophenyl)-2,2',3',9'-tetramethyl-spiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

HRID 1772361Notes

Reaction equation

HRID 1772361 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C:10]3([CH2:25][CH:24]3[CH3:26])[N:9]=2)=[CH:4][CH:3]=1.C(O)[C@H](O)C>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@@:10]3([CH2:25][C@H:24]3[CH3:26])[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 259994R-(-)-1,2-PropanediolHCID 76524868Racemic 4'-(4-chlorophenyl)-2,2',3',9'-tetramethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Product 1

HCID 57405267(1S,2R)-4'-(4-chlorophenyl)-2,2',3',9'-tetramethyl-spiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]

Procedure

A procedure analogous to the scheme set forth for the synthesis of Compound 215 was followed, with the exception that (R)-propane-1,2-diol was used as starting material. LRMS (M+H)+: 383 m/z. 1H NMR (400 MHz, DMSO-d6) δ 7.50 (s, 4H), 3.80 (t, J=6.98 Hz, 1H), 2.55-2.63 (m, 3H), 2.39 (s, 3H), 1.95-2.03 (m, 1H), 1.58 (s, 3H), 1.39 (d, J=5.95 Hz, 1H), 1.05-1.12 (m, 1H), 0.79 (d, J=5.49 Hz, 3H).

Sources & evidence

ORD record
ord-db08a1b93ad94c72a3f8697d10b70cf1
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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