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4-Amino-1-Boc-piperidine → 1,1-Dimethylethyl 4-(7-cyano-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-1-piperidinecarboxylate

HRID 1097978
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HRID 1097978 반응식
Br[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]#[N:14])[C:4]=1[C:5](OC)=[O:6].[NH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1>O1CCCC1.CN(C=O)C>[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:3]2[C:4]=1[C:5](=[O:6])[N:15]([CH:16]1[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:20][CH2:21]1)[CH2:2]2)#[N:14]
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참가 물질

5

반응물 2

HCID 12682914-Amino-1-Boc-piperidineHCID 66812920Methyl 2-(bromomethyl)-6-cyanobenzoate

생성물 1

HCID 668126151,1-Dimethylethyl 4-(7-cyano-1,3-dihydro-1-oxo-2H-isoindol-2-yl)-1-piperidinecarboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of EXAMPLE 6C (300 mg) in tetrahydrofuran (2 mL) and N,N′-dimethylformamide (2 mL) was added tert-butyl 4-aminopiperidine-1-carboxylate (320 mg,) in N,N′-dimethylformamide (2 mL) and tetrahydrofuran (2 mL) at −40° C. The solution was warmed to ambient temperature over 2 hours, and stirred for 16 hours. The solvent was removed, and the concentrate was partitioned between ethyl acetate and water. The extract was washed with brine and concentrated, and the concentrate was purified by flash chromatography on silica gel with 80% ethyl acetate in hexanes.

후처리

  1. customThe solvent was removed
  2. customthe concentrate was partitioned between ethyl acetate and water
  3. washThe extract was washed with brine
  4. concentrationconcentrated
  5. customthe concentrate was purified by flash chromatography on silica gel with 80% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-d66f2dfb232349c19618d4d8d792bef2
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08143284B2

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