Trifluoroacetic acid → 2-(2-(2H-1,2,3-triazol-2-yl)benzyl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41577Notes

Reaction equation

HRID 41577 reaction equation
[N:1]1[N:2]([C:6]2[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=2[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[C:10]2=[O:27])[N:3]=[CH:4][CH:5]=1.C(O)(C(F)(F)F)=O>ClCCl>[N:1]1[N:2]([C:6]2[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=2[CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C:11]3([CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[C:10]2=[O:27])[N:3]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67253417tert-butyl 2-(2-(2H-1,2,3-triazol-2-yl)benzyl)-1-oxo-2,9-diazaspiro[5.5]-undecane-9-carboxylate

Product 1

HCID 672526432-(2-(2H-1,2,3-triazol-2-yl)benzyl)-2,9-diazaspiro[5.5]undecan-1-oneYield 209.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-(2H-1,2,3-triazol-2-yl)benzyl)-1-oxo-2,9-diazaspiro[5.5]-undecane-9-carboxylate (1.76 g, 4.09 mmol) in dichloromethane (15 mL) was added TFA (3.15 mL, 40.9 mmol). The solution was stirred for 25 min at rt. After completion of the reaction the mixture was evaporated to dryness. The residue was dried under high vacuum to yield the title compound as a solid (2.79 g, quant.). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.42 (br s, 2H), 8.11 (s, 2H), 7.64-7.60 (m, 1H), 7.51-7.47 (m, 2H), 7.24 (d, 1H), 4.55 (s, 2H), 3.24-3.18 (m, 2H), 3.13-3.11 (m, 2H), 3.09-2.97 (m, 2H), 2.13-2.04 (m, 2H), 1.82-1.70 (m, 4H), 1.65-1.55 (m, 2H); LCMS RtA=0.60, [M+H]+=326.3].

Workup

  1. customAfter completion of the reaction the mixture
  2. customwas evaporated to dryness
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-7369440098b6424c96e1a77d9a9f6a61
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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