Triphenylphosphine → Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate

HRID 19890

反応式

HRID 19890 の反応式
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[CH:17]=[C:18]([OH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([O:25][C:18]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([CH3:15])[CH:17]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 174123-Methyl-4-nitrophenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 18542679Tert-butyl 4-(3-methyl-4-nitrophenoxy)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Diisopropyl azodicarboxylate (10.56 mL, 1.6 eq.) was added to a cold (0° C.) mixture of 3-methyl-4-nitrophenol (5 g, 1.0 eq.), 1-tert-butyloxycarbonyl-4-hydroxy-piperidine (9.96 g, 1.6 eq.) and triphenylphosphine (13.85 g, 1.6 eq.) in tetrahydrofuran (205 mL). After 1 h stirring, the mixture was evaporated to dryness and dissolved in tert-butylmethylether. The organic phase was washed with 0.5M sodium hydroxide solution and 5% sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The product was recrystallized from methanol to yield 9.498 g (88%) as white crystals. MS (m/e): 336.2 (M, 10%).

後処理

  1. customthe mixture was evaporated to dryness
  2. dissolutiondissolved in tert-butylmethylether
  3. washThe organic phase was washed with 0.5M sodium hydroxide solution and 5% sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe product was recrystallized from methanol
  8. customto yield 9.498 g (88%) as white crystals

出典と根拠

ORDレコード
ord-6faa8a0bc8f0409f90583664eb3f629d
出典データセット
uspto-grants-2010_06
特許番号
US07745479B2

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