tert-Butyl piperazine-1-carboxylate → tert-butyl-4-[2-(1-oxo-3,4-dihydro-1H-isochromen-6-yl)ethyl]piperazine-1-carboxylate

HRID 2173136Notes

Reaction equation

HRID 2173136 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][CH:13]=O)=[CH:9][CH:10]=2)[CH2:5][CH2:4][O:3]1.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][N:25]([CH2:13][CH2:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2](=[O:1])[O:3][CH2:4][CH2:5]3)[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 772306602-(1-Oxoisochroman-6-yl)acetaldehyde

Product 1

HCID 89545536tert-butyl-4-[2-(1-oxo-3,4-dihydro-1H-isochromen-6-yl)ethyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Oxo-3,4-dihydro-1H-isochromen-6-yl)acetaldehyde (2.40 g, 12.6 mmol) was combined with 1-Boc-piperazine (3.53 g, 18.9 mmol) and sodium triacetoxyborohydride (13.4 g, 63.1 mmol) in DCM (90 mL). The reaction mixture was stirred at room temperature overnight. Saturated sodium bicarbonate solution was added and the layers were separated. The organic layer was washed with brine, then dried over MgSO4. The crude product was purified first by MPLC (silica), eluting with 3% of a 10% NH4OH/methanol solution in DCM, then a second MPLC purification eluting with ethyl acetate, to afford the title compound. LCMS: m/z 361 (M+1)+.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified first by MPLC (silica)
  5. washeluting with 3% of a 10% NH4OH/methanol solution in DCM
  6. customa second MPLC purification
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-648ead2cb3ac41ddba16a98e810a2bbd
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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