(3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol → (3aRS,4RS,6SR,7aSR)-6-aminomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol

HRID 1599159Notes

Reaction equation

[N:1]([CH2:4][CH:5]1[CH2:13][CH:12]2[CH:8]([CH2:9][N:10]([C:14](=[O:24])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:11]2)[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])([OH:25])[CH2:6]1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][CH:5]1[CH2:13][CH:12]2[CH:8]([CH2:9][N:10]([C:14](=[O:24])[CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH3:23])[CH2:11]2)[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH3:33])([OH:25])[CH2:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6.05 g of (3aRS,4RS,6SR,7aSR)-6-azidomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol, 0.6 g of 10% palladium on carbon and 300 cm3 of ethanol is heated to 60° C. Hydrogen is bubbled through for 3 hours, and then the reaction mixture is left at 20° C. for 20 hours and then purged with a stream of nitrogen, filtered and concentrated under reduced pressure (2.7 kPa). 5.7 g of (3aRS,4RS,6SR,7aSR)-6-aminomethyl-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]perhydroisoindol-4-ol are obtained in the form of a thick white foam.

Workup

customHydrogen is bubbled through for 3 hours
custompurged with a stream of nitrogen
filtrationfiltered
concentrationconcentrated under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-98f90f39b1db4332a6b84ca6712917e2
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739351

Reaction notes

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