2-[2-(Pyrrolidin-1-yl)phenyl]acetic acid → (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol

HRID 1599154Notes

Reaction equation

HRID 1599154 reaction equation
Cl.[OH:2][CH2:3][CH:4]1[CH2:12][CH:11]2[CH:7]([CH2:8][NH:9][CH2:10]2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])([OH:13])[CH2:5]1.[N:21]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][C:33](O)=[O:34])[CH2:25][CH2:24][CH2:23][CH2:22]1>>[OH:2][CH2:3][CH:4]1[CH2:12][CH:11]2[CH:7]([CH2:8][N:9]([C:33](=[O:34])[CH2:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:10]2)[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])([OH:13])[CH2:5]1

Participants

3

Reactant 2

HCID 230093992-[2-(Pyrrolidin-1-yl)phenyl]acetic acidHCID 67660643(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)perhydroisoindol-4-ol hydrochloride

Product 1

HCID 86752420(3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-olYield 18.3%

Procedure

The procedure is as described for Example 14, starting from 0.73 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)perhydroisoindol-4-ol hydrochloride and 0.68 g of 2-(1-pyrrolidinyl)phenylacetic acid, and gives 0.2 g of (3aRS,4RS,6SR,7aSR)-6-hydroxymethyl-4-(2-fluorophenyl)-2-[2-(1-pyrrolidinyl)phenylacetyl]perhydroisoindol-4-ol in the form of a thick white foam.

Sources & evidence

ORD record
ord-4d4500dcf7a64d14833aaacad3b4172e
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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