Isobutyric Acid → HCID 67538280, compound

HRID 2383060Notes

Reaction equation

HRID 2383060 reaction equation
[NH2:1][CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:10]2[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[C:26](O)(=O)[CH:27]([CH3:29])[CH3:28].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O>[C:22]([O:21][C:19]([N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([CH2:2][NH:1][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:4][CH:5]=2)[CH:10]1[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 6590Isobutyric AcidHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67536297HCID 67536297, compound

Product 1

HCID 67538280HCID 67538280, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 7-(aminomethyl)-1-cyclohexyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (999 mg) was dissolved in methylene chloride. Isobutyric acid (0.33 mL), triethylamine (1.2 mL), and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.32 g) were added thereto, followed by stirring at room temperature for 18 hours. Water was added to the mixture which was then extracted with chloroform. The extract was washed with a 1 M aqueous NaOH solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography to obtain tert-butyl-1-cyclohexyl-7-[(isobutylamino)methyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate (468 mg).

Workup

  1. extractionwas then extracted with chloroform
  2. washThe extract was washed with a 1 M aqueous NaOH solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2783a2258a4048e88a14c1a8ab5d8ff5
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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