Trifluoroacetic acid → 2,8-Diazaspiro[4.5]decan-1-one

HRID 1848552Notes

Reaction equation

HRID 1848552 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:5][CH2:4][NH:3]1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:2]1(=[O:1])[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 45073946tert-Butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 222250112,8-Diazaspiro[4.5]decan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (I-11) (5.0 g, 19.7 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (15.2 mL, 197 mmol) and the resulting solution was stirred at rt for 1 h. After evaporating the volatiles the residue was basified on ion exchange column washed with methanol followed by 1 N ammonia in methanol to give 2,8-diazaspiro[4.5]decan-1-one. LC/MS: (M+1)+: 155.11

Workup

  1. customAfter evaporating the volatiles the residue
  2. washwashed with methanol

Sources & evidence

ORD record
ord-ebdc5bcc151e4928bbabd9bd078892bb
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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