Hydrochloric Acid → (3aRS,4RS,7SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4,7-perhydroisoindolediol

HRID 55425Notes

Reaction equation

[OH:1][C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH:10]2[CH:6]([CH2:7][N:8]([C:11](=[O:21])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[CH2:9]2)[C:5](=[O:22])[CH2:4][CH2:3]1.[BH4-].[Na+].Cl>CO>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:2]1([OH:1])[CH2:3][CH2:4][CH:5]([OH:22])[CH:6]2[CH:10]1[CH2:9][N:8]([C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[CH2:7]2

Participants

Conditions

Temperature: 5 °C

Procedure

To a suspension, cooled to +5° C., of 0.5 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2 -methoxyphenyl)acetyl]-4-perhydroisoindolone in 50 cm3 of methanol is added 0.027 g of sodium borohydride. After stirring for 2 hours at 5° C., 0.2 cm3 of 1N hydrochloric acid is added to the reaction solution which is then concentrated to dryness under reduced pressure. The residue is taken up in 50 cm3 of water and 70 cm3 of dichloromethane. After stirring, the suspension obtained is filtered and the organic phase of the filtrate is washed with water and then dried over. magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). 0.42 g of (3aRS,4RS,7SR,7aSR)-4-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4,7-perhydroisoindolediol is obtained in the form of a white foam.

Workup

concentrationis then concentrated to dryness under reduced pressure
stirringAfter stirring
customthe suspension obtained
filtrationis filtered
washthe organic phase of the filtrate is washed with water
customdried over
concentrationmagnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-9f7c9181175546e69cce68f969952c4a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Reaction notes

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