Triethylamine → tert-Butyl 6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate

HRID 627427Notes

Reaction equation

HRID 627427 reaction equation
Cl.[NH:2]1[C:6]2([CH2:10][CH2:9][NH:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3]1.[C:12]([O:16][C:17](OC([O-])=O)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl.O>[C:12]([O:16][C:17]([N:2]1[C:6]2([CH2:10][CH2:9][NH:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22064466Tert-butyldicarbonateHCID 866866531,7-Diazaspiro[4.4]nonan-6-one hydrochloride

Product 1

HCID 49760540tert-Butyl 6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylateYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,7-diazaspiro[4,4]nonan-6-one hydrochloride (0.98 g, 5.4 mmol) in dichloromethane were added tert-butyldicarbonate (1.41 g, 6.48 mmol) and triethylamine (1.3 g, 13.5 mmol). The resulting solution was stirred overnight at room temperature. The solution was diluted with water and extracted with dichloromethane. The organic phase was separated, dried, filtered and concentrated to afford 6-oxo-1,7-diaza-spiro[4,4]nonan-1-carboxylic acid tert-butyl ester product as white powder (1.3 g) in 100% yield and used directly without further purification. 1H NMR (400 MHz, CD2Cl2) δ 6.13-5.74 (br, 1H), 3.59-3.20 (m, 4H), 2.75-2.49 (m, 1H), 2.16-1.76 (m, 5H), 1.43 (s, 3H), 1.42 (s, 6H). MS m/z 241.2 (M+H)+

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phase was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d802bb7a4c34443bac9bd999e9c43860
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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