Dimethylformamide → HCID 86705548、化合物

HRID 2279563ノート

反応式

HRID 2279563 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=2)(C(O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[N:43]([CH:45]=[O:46])C>CCOC(C)=O>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([N:43]=[C:45]=[O:46])[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]2)[CH:22]=[CH:21][C:20]=1[Cl:23]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 68294367HCID 68294367、化合物

生成物 1

HCID 86705548HCID 86705548、化合物収率 91%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 358 (187 mg, 0.4997 mmol) in DMF (1.5 mL) at RT under nitrogen was added TEA (167.1 μL, 1.199 mmol) neat via syringe followed by DPPA (129.6 μL, 0.5996 mmol) neat by syringe. The solution was stirred for 2 h at RT then warmed to 60° C. After 3 h at 60° C., the reaction was cooled to RT and diluted to 30 mL with EtOAc. The organic extract was washed with H2O (3×30 mL) and brine (1×30 mL). The organics were dried (MgSO4), filtered and concentrated to afford 170 mg (91%) of tert-butyl 4-(3,4-dichlorophenyl)-4-isocyanatopiperidine-1-carboxylate (360) as a clear oil.

後処理

  1. temperaturethen warmed to 60° C
  2. waitAfter 3 h at 60° C.
  3. temperaturethe reaction was cooled to RT
  4. extractionThe organic extract
  5. washwas washed with H2O (3×30 mL) and brine (1×30 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-8458255fded8411681fa1631e944df46
出典データセット
uspto-grants-2015_09
特許番号
US09133187B2

反応ノート

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