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

HRID 451706
ノート
印刷プレビュー

反応式

HRID 451706 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360
Sodium chloride; water
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-888ea3d6ab424c2abe60b9dddfb1c9a2
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08487108B2

反応ノート

読み込み中…

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