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Benzyl chloroformate → 1-Benzyl 6-(tert-butyl) 1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

HRID 1912402
ノート
印刷プレビュー

反応式

HRID 1912402 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH2:17])([CH2:14][CH2:15]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br.Cl[C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44]>ClCCl.O.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([N:17]([C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])[CH2:15][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10387Benzyl chloroformateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58293371HCID 58293371、化合物

生成物 1

HCID 582933361-Benzyl 6-(tert-butyl) 1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
HCID 8471Triethylamine溶媒2 回

実験手順

To a solution of an optically-active compound of 3-amino-3-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester (6.46 g), triphenylphosphine (12.5 g) and triethylamine (13.3 ml) in dichloromethane (226 ml) cooled to 0° C. was added carbon tetrabromide (15.8 g). The reaction mixture was stirred at room temperature for 40 minutes and cooled to 0° C. again. Then, thereto were added triethylamine (5.5 ml) and benzyl chloroformate (4.9 ml), and the mixture was stirred for 3.5 hours at room temperature. To the mixture was added water (200 ml), and the mixture was extracted with chloroform (100 ml). The organic layer was washed with saturated aqueous sodium chloride solution, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to give the titled compound (5.35 g).

後処理

  1. temperaturecooled to 0° C. again
  2. stirringthe mixture was stirred for 3.5 hours at room temperature
  3. extractionthe mixture was extracted with chloroform (100 ml)
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-dc0c4a81bcfc485ea2fba4e1a96c98b2
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609647B2

反応ノート

読み込み中…

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