Diisopropylethylamine → HCID 66639097, compound

HRID 1094257Notes

Reaction equation

HRID 1094257 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[O:15]1[C:19]2=[CH:20][CH:21]=[CH:22][C:23]([C:24](O)=[O:25])=[C:18]2[CH:17]=[CH:16]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CC(=O)OCC.CC(=O)OCC.CCCCCCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:24]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]3[O:15][CH:16]=[CH:17][C:18]=23)=[O:25])[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 2724699PyBOPHCID 223241171-Benzofuran-4-carboxylic acid

Product 1

HCID 66639097HCID 66639097, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 21899848Ethylacetate heptaneSolvent

Procedure

A mixture of (R)-3-amino-1-N-Boc-piperidine (1 g), benzofuran-4-carboxylic acid (809 mg), PyBOP (2.6 g), DIEA (1.96 mL) in dry DMF (10 mL) was stirred at RT under nitrogen for 20 h. The reaction mixture was diluted with EA, washed with water. The aqueous phase was extracted twice with EA, the combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to yield a crude light brown oil. FC (EA/n-heptane: 1/1 to EA) gave 1.41 g (82%) of the title compound as an oil.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase was extracted twice with EA
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude light brown oil

Sources & evidence

ORD record
ord-05d0f243d2de4e9fa5effca8a0ce180a
Source dataset
uspto-grants-2012_03
Patent number
US08133901B2

Reaction notes

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