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

HRID 1850638Notes

Reaction equation

HRID 1850638 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-1389c5024e194f31946780253668b876
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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