tert-Butyl piperazine-1-carboxylate → HCID 89501024, compound

HRID 1467808Notes

Reaction equation

HRID 1467808 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C:5]([CH3:23])([CH3:22])[N:6]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7]2.CC([O-])(C)C.[Na+].[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:39]([O:38][C:36]([N:30]1[CH2:35][CH2:34][N:33]([C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH2:4][C:5]([CH3:23])([CH3:22])[N:6]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:7]3)[CH2:32][CH2:31]1)=[O:37])([CH3:42])([CH3:40])[CH3:41]

Participants

7

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxideHCID 89501029HCID 89501029, compound

Product 1

HCID 89501024HCID 89501024, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To 78A (600 mg, 1.60 mmol) in toluene (5 mL) was added NaOtBu (215 mg, 2.24 mmol), tert-butyl piperazine-1-carboxylate (358 mg, 1.92 mmol), Pd2(dba)3 (3.6 mg, 0.004 mmol) and BINAP (7.4 mg, 0.012 mmol). The reaction mixture was heated at 100° C. in a sealed tube. After 18 h, the reaction was cooled to rt, quenched with H2O, extracted with EtOAc twice, the combined organics were washed with H2O, brine, dried over anhydrous Na2SO4, filtered and concentrated. Purification by silica gel column chromatography afforded 78B (500 mg, 67%) as a green liquid. MS (ESI) m/z: 480.4 (M+H)+.

Workup

  1. temperaturethe reaction was cooled to rt
  2. customquenched with H2O
  3. extractionextracted with EtOAc twice
  4. washthe combined organics were washed with H2O, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-7f4990fd9f8d4beabbc9263edb3ad309
Source dataset
uspto-grants-2015_04
Patent number
US09000172B2

Reaction notes

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