Trifluoroacetic acid → Spiro[isoindoline-1,4'-piperidin]-3-one

HRID 1424583Notes

Reaction equation

HRID 1424583 reaction equation
COC1C=CC(C[N:8]2[C:16]3([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:29])=CC=1.C(O)(C(F)(F)F)=O>>[NH:19]1[CH2:20][CH2:21][C:16]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:29])[NH:8]2)[CH2:17][CH2:18]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58137355Tert-butyl 2-(4-methoxybenzyl)-3-oxospiro[isoindoline-1,4'-piperidine]-1'-carboxylate

Product 1

HCID 15548169Spiro[isoindoline-1,4'-piperidin]-3-one

Procedure

Tert-butyl 2-(4-methoxybenzyl)-3-oxospiro[isoindoline-1,4′-piperidine]-1′-carboxylate (50 mg, 0.12 mmol, 1.0 equiv) and TFA (7 mL) were heated to 75° C. for 19 h. After this time LC-MS showed removal of the Boc- and p-methoxybenzyl groups. The mixture was concentrated to leave crude spiro[isoindoline-1,4′-piperidin]-3-one which was used directly.

Workup

  1. customremoval of the Boc- and p-methoxybenzyl groups
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-58852a0a1e8b42bc8ed34ccc65b659c1
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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