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Sodium triacetoxyborohydride → 1-({4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-5-(methyloxy)-3,4-dihydro-1H-isochromene-6-carbonitrile

HRID 1187144
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HRID 1187144 반응식
[CH3:1][O:2][C:3]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][O:7][CH:8]2[CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[CH3:22][C:23]1[C:31]2[CH2:30][O:29][C:28](=[O:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH:34]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:22][C:23]1[C:31]2[CH2:30][O:29][C:28](=[O:32])[C:27]=2[CH:26]=[CH:25][C:24]=1[CH2:33][CH2:34][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH:8]2[C:9]3[C:4](=[C:3]([O:2][CH3:1])[C:12]([C:13]#[N:14])=[CH:11][CH:10]=3)[CH2:5][CH2:6][O:7]2)[CH2:17][CH2:18]1
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참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydrideHCID 675156135-(methyloxy)-1-(piperazin-1-ylmethyl)-3,4-dihydro-1H-isochromene-6-carbonitrileHCID 772312602-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde2회

생성물 1

HCID 498016271-({4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-5-(methyloxy)-3,4-dihydro-1H-isochromene-6-carbonitrile

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

To a solution of 5-(methyloxy)-1-(piperazin-1-ylmethyl)-3,4-dihydro-1H-isochromene-6-carbonitrile (0.04 mmol) in 5 mL of DCM was added (4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (from Step B, Intermediate 17, 11 mg, 0.06 mmol) and NaBH(OAc)3 (34 mg, 0.16 mmol), 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 1-({4-[2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}methyl)-5-(methyloxy)-3,4-dihydro-1H-isochromene-6-carbonitrile.

후처리

  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

출처 및 근거

ORD 기록
ord-3b65ebc36cfb409a91d94a13d6c89273
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673920B2

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