Sodium triacetoxyborohydride → HCID 66646349, compound

HRID 1187145Notes

Reaction equation

HRID 1187145 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([CH2:14][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[O:7][CH2:6][CH2:5]2.[Br:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[CH:28]([CH:34]=O)[O:27][CH2:26][CH2:25]2.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([CH2:14][N:15]1[CH2:16][CH2:17][N:18]([CH2:34][CH:28]3[C:29]4[C:24](=[CH:23][C:22]([Br:21])=[C:31]([O:32][CH3:33])[CH:30]=4)[CH2:25][CH2:26][O:27]3)[CH2:19][CH2:20]1)[O:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 59568680HCID 59568680, compoundHCID 86647314HCID 86647314, compound

Product 1

HCID 66646349HCID 66646349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-{[6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromen-1-yl]methyl}piperazine (100 mg, 0.3 mmol) in 5 mL of DCM was added 6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromene-1-carbaldehyde (81 mg, 0.30 mmol) and NaBH(OAc)3 (127 mg, 0.6 mmol). The mixture was stirred at room temperature overnight. The reaction mixture 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 1,4-bis{[6-bromo-7-(methyloxy)-3,4-dihydro-1H-isochromen-1-yl]methyl}piperazine.

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-2b784929c07e4918901b7ad2fd56f2a9
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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