Potassium Cyanide → HCID 67660705, compound

HRID 1599149Notes

Reaction equation

C1(C)C=CC(S(O[CH2:11][CH:12]2[CH2:20][CH:19]3[CH:15]([CH2:16][N:17]([C:21](=[O:37])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:18]3)[C:14]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[F:45])([OH:38])[CH2:13]2)(=O)=O)=CC=1.[C-:47]#[N:48].[K+]>>[C:47]([CH2:11][CH:12]1[CH2:20][CH:19]2[CH:15]([CH2:16][N:17]([C:21](=[O:37])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:18]2)[C:14]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])([OH:38])[CH2:13]1)#[N:48]

Participants

Reactant 2

HCID 9032Potassium Cyanide

HCID 86752417HCID 86752417, compound

Product 1

HCID 67660705HCID 67660705, compoundYield 44%

Procedure

The procedure is as described for Example 13, starting from 1.67 g of (3aRS,4RS,6RS,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-(2-benzyloxyphenylacetyl)perhydroisoindol-4-ol and 0.104 g of potassium cyanide, and gives 0.35 g of (3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-(2-benzyloxyphenylacetyl)perhydroisoindol-4-ol in the form of a thick pink foam.

Sources & evidence

ORD record: ord-7e939f163bdc4ca38865448a844e4fe5
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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