Phthalimide → N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide

HRID 602121ノート

反応式

HRID 602121 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([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:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][N:40]2[C:39](=[O:41])[C:38]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]3[C:36]2=[O:46])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23521554Tert-butyl 3-(hydroxymethyl)azepane-1-carboxylate

生成物 1

HCID 58992706N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide収率 72%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1-(tert-Butoxycarbonyl)perhydroazepin-3-yl methanol (1.13 g, 4.93 mmol) was dissolved in tetrahydrofuran (10 mL). To this solution, triphenylphosphine (1.60 g, 5.92 mmol) and phthalimide (871 mg, 5.92 mmol) were added and the mixture was stirred at room temperature for 5 min. A 40% toluene solution of diethyl azodicarboxylate (3.23 mL, 7.40 mmol) was then added and the mixture was stirred at room temperature for 4 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.27 g (72%) of the desired compound as a colorless powder.

後処理

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed with brine
  4. dry with materialwas dried over magnesium sulfate
  5. customfollowed by evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

出典と根拠

ORDレコード
ord-5a699c5b9dd144ba9de0c8e26f7334a9
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

反応ノート

読み込み中…