HCID 67661848, compound → HCID 67660614, compound

HRID 1599140Notes

Reaction equation

HRID 1599140 reaction equation
[C:1]([CH2:3][C@@H:4]1[CH2:12][C@@H:11]2[C@@H:7]([CH2:8][N:9]([C:13](=[O:29])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21]CC3C=CC=CC=3)[CH2:10]2)[C@@:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])([OH:30])[CH2:5]1)#[N:2].[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[C:1]([CH2:3][C@@H:4]1[CH2:12][C@@H:11]2[C@@H:7]([CH2:8][N:9]([C:13](=[O:29])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[CH2:10]2)[C@@:6]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH3:38])([OH:30])[CH2:5]1)#[N:2]

Participants

5

Reactant 2

HCID 67661848HCID 67661848, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67660614HCID 67660614, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(3aS,4S,6S,7aR)-6-Cyanomethyl-2-[(2-hydroxyphenyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol is obtained by proceeding as described in Example 4, from 1.3 g of (3aS,4S,6S,7aR)-6-cyanomethyl-2-[(2-benzyloxyphenyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol, 130 cm3 of ethanol, 0.3 g of 20% palladium hydroxide on carbon black, and hydrogen. Purification by chromatography gives 0.60 g of (3aS,4S,6S,7aR)-6-cyanomethyl-2-[(2-hydroxyphenyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol in the form of a thick white foam.

Workup

  1. customPurification by chromatography

Sources & evidence

ORD record
ord-744aadd5b0ee4f4a99996f40723e082e
Source dataset
uspto-grants-1998_04
Patent number
US05739351

Reaction notes

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