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Triethylammonium formate → (R)-tert-butyl 3-(2,3-difluoro-6-methylbenzoyl)piperidine-1-carboxylate

HRID 451706
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HRID 451706 반응식
[F:1][C:2]1[C:22]([F:23])=[C:21]([Si](C)(C)C)[CH:20]=[C:19]([CH3:28])[C:3]=1[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].CCN(CC)CC.C(O)=O>C1COCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:22]([F:23])=[CH:21][CH:20]=[C:19]([CH3:28])[C:3]=1[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:7]1)=[O:5]
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참가 물질

5

반응물 2

HCID 11084032Triethylammonium formateHCID 59201562(R)-tert-butyl 3-(2,3-difluoro-6-methyl-4-(trimethylsilyl)benzoyl)piperidine-1-carboxylate

생성물 1

HCID 59201542(R)-tert-butyl 3-(2,3-difluoro-6-methylbenzoyl)piperidine-1-carboxylate수율 61%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 57417360
Sodium chloride; water
용매

실험 절차

To a solution of (R)-tert-butyl 3-(2,3-difluoro-6-methyl-4-(trimethylsilyl)benzoyl)piperidine-1-carboxylate (2 g, 4.9 mmol) in THF (20 mL) was added TEAF (0.22 g, 1.5 mmol) in THF (5 mL) at 0° C. The mixture was stirred for 4 h, after which brine was added, and the mixture was extracted with Et2O. The organic layer was washed with brine and dried over Na2SO4, concentrated. The residue was purified by column chromatography on silica gel to afford (R)-tert-butyl 3-(2,3-difluoro-6-methylbenzoyl)piperidine-1-carboxylate (1 g, 61%). 1H-NMR δ 7.07 (m, 1H), 6.90 (m, 1H), 4.10 (m, 2H), 3.92 (m, 2H), 2.21 (s, 3H), 1.97 (m, 2H), 1.60 (m, 4H), 1.49 (s, 9H), 1.30 (m, 3H).

후처리

  1. extractionthe mixture was extracted with Et2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-888ea3d6ab424c2abe60b9dddfb1c9a2
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08487108B2

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