Sodium triacetoxyborohydride → 7-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1466153Notes

Reaction equation

HRID 1466153 reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][C:16]2[CH:15]=[C:14]([C:18]#[N:19])[CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1.[O:20]=[C:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][CH:31]=O)=[CH:29][C:24]=2[CH2:23][O:22]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][N:6]([CH2:31][CH2:30][C:28]2[CH:27]=[CH:26][C:25]3[C:21](=[O:20])[O:22][CH2:23][C:24]=3[CH:29]=2)[CH2:5][CH2:4][N:3]1[CH:8]1[CH2:17][C:16]2[CH:15]=[C:14]([C:18]#[N:19])[CH:13]=[CH:12][C:11]=2[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehydeHCID 895251235,6,7,8-Tetrahydro-7-(2-oxo-1-piperazinyl)-2-naphthalenecarbonitrile

Product 1

HCID 895334917-{2-Oxo-4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 7-(2-Oxopiperazin-1-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (100 mg, 0.39 mmol) in 10 mL of anhydrous DCM was added (1-Oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (69 mg, 0.39 mmol), NaBH(OAc)3 (330 mg, 1.56 mmol) and the mixture was stirred at room temperature overnight. DCM was added, and the mixture was washed with brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give the desired product. 1H-NMR (400 MHz, CDCl3) δ ppm 7.79 (d, J=7.5 Hz, 1H), 7.27-7.35 (m, 4H), 7.12 (d, J=8.3 Hz, 1H), 5.23 (s, 2H), 4.74-4.85 (m, 1H), 3.17-3.34 (m, 4H), 2.64-2.95 (m, 10H), 1.74-1.95 (m, 2H).

Workup

  1. washthe mixture was washed 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-30396f76c2774b3c9fdc27ccd18eaf28
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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