tert-Butyl 4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidine-1-carboxylate → 2'-Oxo-N-(piperidin-4-ylmethyl)spiro[cyclopentane-1,3'-indole]-1'(2'H)-carboxamide

HRID 733086Notes

Reaction equation

HRID 733086 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]1)=[O:16]>Cl.CO>[O:1]=[C:2]1[C:10]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]([NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1)=[O:16]

Participants

4

Reactant 1

HCID 86607413tert-Butyl 4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidine-1-carboxylate

Product 1

HCID 672325932'-Oxo-N-(piperidin-4-ylmethyl)spiro[cyclopentane-1,3'-indole]-1'(2'H)-carboxamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

tert-Butyl 4-({[(2′-oxospiro[cyclopentane-1,3′-indol]-1′(2′H)-yl)carbonyl]amino}methyl)piperidine-1-carboxylate (750 mg, 1.8 mmol, step 1 of Example 2) was dissolved in 10% HCl in methanol (20 mL) and the mixture was stirred for 7 h at room temperature. Concentrated gave a colorless oil, which was chromatographed on a column of silica gel eluting with CH2Cl2/methanol/NH4OH (12/11/0.1) to give 570 mg (quant.) of the title compound as colorless oil.

Workup

  1. concentrationConcentrated
  2. customgave a colorless oil, which
  3. customwas chromatographed on a column of silica gel eluting with CH2Cl2/methanol/NH4OH (12/11/0.1)

Sources & evidence

ORD record
ord-1c1af8a725f140bc95381e265a129d32
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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