Diisopropylethylamine → Tert-butyl 9-(4-fluoro-3-methoxybenzoyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate

HRID 2387285Notes

Reaction equation

HRID 2387285 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:2]1.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=1[O:29][CH3:30].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:9]2[CH2:10][CH2:11][C:6]3([CH2:1][CH2:2][N:3]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4][CH2:5]3)[CH2:7][CH2:8]2)=[O:25])=[CH:22][C:21]=1[O:29][CH3:30]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5984364-Fluoro-3-methoxybenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 67523793Tert-butyl 9-(4-fluoro-3-methoxybenzoyl)-3,9-diazaspiro[5.5]undecane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate (30 mg, 0.12 mmol; U.S. Pat. No. 5,451,578), 4-fluoro-3-methoxybenzoic acid (20 mg, 0.12 mmol; Aldrich), N,N-diisopropylethylamine (0.025 mL, 0.14 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 54 mg, 0.14 mmol; Aldrich) in anhydrous N,N-dimethylformamide (1 mL) was stirred overnight at room temperature. The reaction was diluted with water (10 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to provide the title compound which was carried on to the next step without further purification.

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd562226ad5b4f5e9346f07c30a73bcf
Source dataset
uspto-grants-2012_09
Patent number
US08268853B2

Reaction notes

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