Potassium Cyanide → HCID 67660605, compound

HRID 1599145Notes

Reaction equation

[C-:1]#[N:2].[K+].C1(C)C=CC(S(O[CH2:14][C@H:15]2[CH2:23][C@@H:22]3[C@@H:18]([CH2:19][N:20]([C:24](=[O:35])[C@H:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[O:33][CH3:34])[CH3:26])[CH2:21]3)[C@@:17]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[F:43])([OH:36])[CH2:16]2)(=O)=O)=CC=1>CS(C)=O.ClCCl>[C:1]([CH2:14][C@@H:15]1[CH2:23][C@@H:22]2[C@@H:18]([CH2:19][N:20]([C:24](=[O:35])[C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[CH3:26])[CH2:21]2)[C@@:17]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])([OH:36])[CH2:16]1)#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

0.35 g of potassium cyanide is added at room temperature to a solution of 1.55 g of (3aS,4S,6S,7aR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol in 15 cm3 of dimethyl sulphoxide. The reaction mixture is stirred at 50° C. for 18 hours and then diluted with 100 cm3 of dichloromethane, and the organic phase is washed with twice 50 cm3 of water then with 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). Recrystallization from diisopropyl ether gives 1.74 g of (3aS,4S,6S,7aR)-6-cyanomethyl-4-(2-fluorophenyl)-2-[(S)-2-(2-methoxyphenyl)propionyl]perhydroisoindol-4-ol in the form of white crystals melting at 182° C.

Workup

washthe organic phase is washed with twice 50 cm3 of water
dry with materialwith 50 cm3 of saturated aqueous sodium chloride solution, dried over magnesium sulphate
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customRecrystallization from diisopropyl ether

Sources & evidence

ORD record: ord-d521f1e6d81244aabdf8644c3ccd470f
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

Loading…