1-Tetralone → Ethyl 1-oxo-3,4-dihydro-1H-spiro[naphthalene-2,4'-piperidine]-1'-carboxylate

HRID 713406Notes

Reaction equation

HRID 713406 reaction equation
[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[CH2:12]([O:14][C:15](=[O:23])[N:16]([CH2:20][CH2:21]Br)[CH2:17][CH2:18]Br)[CH3:13].[H-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[O:10]=[C:9]1[C:11]2([CH2:21][CH2:20][N:16]([C:15]([O:14][CH2:12][CH3:13])=[O:23])[CH2:17][CH2:18]2)[CH2:1][CH2:2][C:3]2[C:8]1=[CH:7][CH:6]=[CH:5][CH:4]=2

Participants

6

Reactant 3

HCID 107241-TetraloneHCID 24758Sodium hydrideHCID 10924683Ethyl bis(2-bromoethyl)carbamate

Product 1

HCID 53766172Ethyl 1-oxo-3,4-dihydro-1H-spiro[naphthalene-2,4'-piperidine]-1'-carboxylateYield 14.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of α-tetralone (289 mg, 1.98 mmol) and bis-(2-bromo-ethyl)-carbamic acid ethyl ester (600 mg, 1.98 mmol) in DMF (2 mL) at 50° C. was added NaH (119 mg, 4.95 mmol) by small portions. After being stirred at 50° C. for 12 h, the reaction was cooled to 25° C. The reaction mixture was diluted with 15 mL of ethyl acetate and washed twice with 10 mL of water, dried over Na2SO4 and concentrated. The crude product was purified via flash chromatography (gradient of 85:15 to 60:40 heptane/ethyl acetate over 20 min) to give the title compound (85 mg, 0.296 mmol) as a white solid. MS calculated for C17H22NO3 288.4. found (ESI) m/z 288.7 (M+H)+, retention time 1.58 min.

Workup

  1. temperaturethe reaction was cooled to 25° C
  2. washwashed twice with 10 mL of water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified via flash chromatography (gradient of 85:15 to 60:40 heptane/ethyl acetate over 20 min)

Sources & evidence

ORD record
ord-4939f8f1f1bc49619a99457b5ebc4ce4
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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