tert-Butyl 4-{[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate → HCID 11997973, compound

HRID 733085Notes

Reaction equation

HRID 733085 reaction equation
[O:1]=[C:2]1[C:10]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]([NH:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2([C:32]([O:34]C(C)(C)C)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:21][CH2:20]1)=[O:16]>C(Cl)Cl.FC(F)(F)C(O)=O>[O:1]=[C:2]1[C:10]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]([NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:26]2([C:32]([OH:34])=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH2:23][CH2:24]1)=[O:16]

Participants

4

Reactant 1

HCID 68472179tert-Butyl 4-{[4-({[(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 11997973HCID 11997973, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl 4-{[4-({[(2′-oxospiro[cyclopentane-1,3′-indol]-1′(2′H)-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (2.3 g, 4.38 mmol, step 6 of Example 1) in CH2Cl2 (14 mL), trifluoroacetic acid (18 mL) was added at room temperature, and the mixture was stirred overnight at room temperature. The mixture was concentrated to give yellow oil, CH2Cl2 (200 mL) was added and washed with sat. NaHCO3 aq. (80 mL), dried over MgSO4, filtered and concentrated gave a syrup, which was chromatographed on a column of silica gel eluting with CH2Cl2/methanol (15:1) to give 2.1 g (quant.) of the title compound as white solid. Recrystallization from ethyl acetate/n-heptane gave white powder.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give yellow oil, CH2Cl2 (200 mL)
  3. additionwas added
  4. washwashed with sat. NaHCO3 aq. (80 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customgave a syrup, which
  9. customwas chromatographed on a column of silica gel eluting with CH2Cl2/methanol (15:1)

Sources & evidence

ORD record
ord-137f7e4ac60b412e8b284746e6b37638
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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