Hydrochloride methanol → 4-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21173Notes

Reaction equation

C(/S([O:12][C:13]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:26][CH:25]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:45])(=O)=O)=C\C1C=CC=CC=1.Cl.CO>>[OH:12][C:13]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[C:24]3[C:29]([CH:30]=2)=[CH:28][C:27]([CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:26][CH:25]=3)=[C:18]2[C:14]=1[CH2:15][NH:16][C:17]2=[O:45]

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 866282764-(trans-beta-Styrenesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

Product 1

HCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneYield 56.8%

Procedure

In a similar manner to Step 2 of Example 233, 4-(trans-β-styrenesulfonyloxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0770 g, 0.0122 mmol) was treated with 10% hydrogen chloride-methanol solution (0.650 mL) to obtain Compound 276 (0.00320 g, yield 49%).

Sources & evidence

ORD record: ord-fc094dff169440528470cc6234db27fb
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Reaction notes

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