tert-Butyl piperazine-1-carboxylate → tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

HRID 2173286Notes

Reaction equation

HRID 2173286 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH:12]=O)[O:7][CH2:6][CH2:5]2.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([CH2:12][N:26]1[CH2:25][CH2:24][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:28][CH2:27]1)[O:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 772312476-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde

Product 1

HCID 68433391tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-bromo-5-methoxy-3,4-dihydro-1H-isochromene-1-carbaldehyde (230 mg, 0.85 mmol) in 10 mL of DCM was added Boc-piperazine (189 mg, 1.02 mmol) and NaBH(OAc)3 (720 mg, 3.4 mmol), and the mixture was stirred at room temperature overnight. The reaction was diluted with DCM, and washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give tert-butyl 4-[(6-bromo-5-methoxy-3,4-dihydro-1H-isochromen-1-yl)methyl]piperazine-1-carboxylate.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-236ecfce58324480921caf4c5765da9a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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