Potassium Cyanide → (3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol

HRID 1599152Notes

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

Participants

Reactant 2

HCID 9032Potassium Cyanide

HCID 86752419(3aRS,4RS,6SR,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol

Product 1

HCID 86752418(3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-olYield 45.1%

Procedure

The procedure is as described for Example 13, starting from 0.07 g of (3aRS,4RS,6SR,7aSR)-6-p-toluenesulphonyloxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol and 0.015 g of potassium cyanide, and gives 0.024 g of (3aRS,4RS,6SR,7aSR)-6-cyanomethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol in the form of a thick white foam.

Sources & evidence

ORD record: ord-9687b154d19e4cb891aff7b683d2e64e
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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