Trifluoroacetic acid → 1,9-Diazaspiro[5.5]undecan-2-one

HRID 41558Notes

Reaction equation

HRID 41558 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)[NH:3]1.C(O)(C(F)(F)F)=O>ClCCl>[NH:3]1[C:4]2([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:5][CH2:6][CH2:7][C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44118856tert-Butyl 2-oxo-1,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 229755861,9-Diazaspiro[5.5]undecan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-oxo-1,9-diazaspiro[5.5]undecane-9-carboxylate [1031927-12-4] (920 mg, 3.26 mmol) in dichloromethane (10 mL) was added TFA (2.53 mL, 32.6 mmol). The solution was stirred for 40 min at rt. After completion of the reaction the mixture was evaporated under reduced pressure and dried under high vacuum (1.90 g, 100%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.59-8.35 (m, 2H), 7.83 (s, 1H), 3.27-3.14 (m, 2H), 3.12-2.98 (m, 2H), 2.17-2.04 (m, 2H), 1.80-1.57 (m, 8H); LCMS RtA=0.20 min, [M+H]+=169.2].

Workup

  1. customAfter completion of the reaction the mixture
  2. customwas evaporated under reduced pressure
  3. customdried under high vacuum (1.90 g, 100%)
  4. custom[1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.59-8.35 (m, 2H), 7.83 (s, 1H), 3.27-3.14 (m, 2H), 3.12-2.98 (m, 2H), 2.17-2.04 (m, 2H), 1.80-1.57 (m, 8H); LCMS RtA=0.20 min, [M+H]+=169.2]

Sources & evidence

ORD record
ord-03c164b82c9e4e11948e70ece3956789
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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