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Tert-butyl 4-hydroxypiperidine-1-carboxylate → 1,1-Dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate

HRID 362785
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인쇄 미리보기

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HRID 362785 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH2:15][C:16]1[C:21]2[CH2:22][CH2:23][O:24][C:20]=2[C:19]([C:25](Cl)=[O:26])=[CH:18][C:17]=1[Cl:28]>CN(C)C1C=CN=CC=1.ClCCl>[NH2:15][C:16]1[C:21]2[CH2:22][CH2:23][O:24][C:20]=2[C:19]([C:25]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[O:26])=[CH:18][C:17]=1[Cl:28]
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참가 물질

5

반응물 2

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 539800704-Amino-5-chloro-2,3-dihydro-7-benzofurancarbonyl chloride

생성물 1

HCID 543178411,1-Dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate수율 59.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344
Dichloromethane
용매
2회

실험 절차

A solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (4.02 g) and N,N-dimethyl-4-pyridinamine (3.7 g) in dichloromethane (200 ml) was stirred at room temperature. A solution of intermediate (7) (4.8 g) in CH2Cl2 (200 ml) was poured into the solution. The reaction mixture was stirred for 3 hours at room temperature. The mixture was washed with water, a 5% NaOH solution and again water. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated. The residue (7.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2). The pure fractions were collected and the solvent was evaporated, yielding 4.7 g of 1,1-dimethylethyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]oxy]-1-piperidinecarboxylate (59%) (intermediate 8).

후처리

  1. washThe mixture was washed with water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (7.4 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 98/2)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-93e9d805ef41497bb90b16380ca33c64
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05872131

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