tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecane-9-carboxylate → 1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one

HRID 41564Notes

Reaction equation

HRID 41564 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[N:3]1[CH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][N:25]2[S:30]([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>ClCCl.C(O)(C(F)(F)F)=O>[S:30]([N:25]1[C:26]2[C:22](=[C:21]([CH2:20][N:3]3[C:4]4([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]4)[CH2:5][CH2:6][CH2:7][C:2]3=[O:1])[CH:29]=[CH:28][CH:27]=2)[CH:23]=[CH:24]1)([C:33]1[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=1)(=[O:31])=[O:32]

Participants

4

Reactant 1

HCID 67252784tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 672515941-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-oneYield 116%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of tert-butyl 2-oxo-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecane-9-carboxylate (0.12 g, 0.21 mmol) in dichloromethane (5.0 mL), TFA (0.5 mL) was added at 0° C. and the reaction mixture was stirred for 16 h at rt under a nitrogen atmosphere. The reaction mixture was concentrated to yield the title compound as colourless oil (0.11 g, 95%) which was used in the next step.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1b823fdffd864b5c81701c432c90458e
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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