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Acetic Acid → Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate

HRID 1930724
ノート
印刷プレビュー

反応式

HRID 1930724 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.N1([C:30](=[O:38])[CH2:31][CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][O:34]2)C=CN=C1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:11]=[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]1[C:30](=[O:38])[CH2:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2733832Lithium hexamethyldisilazaneHCID 593337451-(1H-imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one

生成物 1

HCID 59333690Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate収率 38.9%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 1140Toluene溶媒2 回

実験手順

Lithium bis(trimethylsilyl)amide (2.231 ml, 11.88 mmol) was added to a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (1.127 g, 5.66 mmol) in toluene (3 mL) at 0° C. and the resulting mixture was stirred for 2 minutes. 1-(1H-Imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one (1.099 g, 5.66 mmol) in toluene (1 mL) was added and the reaction mixture was stirred for 5 minutes before it was quenched with acetic acid (0.972 ml, 16.97 mmol) in water (4 mL). The organic layer was separated and purified by silica flash chromatography using a gradient of ethyl acetate in heptane (0 to 40%) giving tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate (0.717 g, 38.9%) as the product.

後処理

  1. stirringthe reaction mixture was stirred for 5 minutes before it
  2. customThe organic layer was separated
  3. custompurified by silica flash chromatography

出典と根拠

ORDレコード
ord-566de2f90d7f433e9eeefc5257f1e99b
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08188101B2

反応ノート

読み込み中…

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