Triethylamine → Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylate

HRID 1959421Notes

Reaction equation

HRID 1959421 reaction equation
[CH2:1]1[C:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]1.CCN(CC)CC.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(Cl)Cl>[C:24]([N:7]1[CH2:6][C:5]2([CH2:1][CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]2)[CH2:9][CH2:8]1)(=[O:27])[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 23282813tert-Butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate

Product 1

HCID 66745092Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of tert-butyl 3,7-diazaspiro[4.4]nonane-3-carboxylate (127 mg, 0.56 mmol) in anhydrous DCM (1 mL), cooled in an ice water bath was added Et3N (57 mg, 78 μL, 0.56 mmol), followed by the addition of propanoyl chloride (57 mg, 54 μL, 0.62 mmol) as a solution in DCM (0.2 mL). The reaction mixture was stirred for 20 minutes, diluted with DCM and was washed with 1M HCl (×2) and brine (×1). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl 3-propanoyl-3,7-diazaspiro[4.4]nonane-7-carboxylate (154 mg, 97%) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 3.73-3.11 (m, 8H), 2.34-2.17 (m, 2H), 1.97-1.70 (m, 4H), 1.46 (s, 9H), 1.16 (t, J=7.4 Hz, 3H). LC/MS m/z 283.5 [M+H]+.

Workup

  1. washwas washed with 1M HCl (×2) and brine (×1)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b97e9dcaae534d38b7fecec4fb617833
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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