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Triphenylphosphine → 3-tert-butyl-1-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)-1H-pyrazol-5-amine

HRID 630862
ノート
印刷プレビュー

反応式

HRID 630862 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2O)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][CH2:44][CH2:45][OH:46].N(C(OCC)=O)=NC(OCC)=O>C1COCC1.O>[C:14]([C:4]1[CH:3]=[C:2]([NH2:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:46][CH2:45][CH2:44][O:43][CH:38]3[CH2:39][CH2:40][CH2:41][CH2:42][O:37]3)[CH:8]=2)[N:5]=1)([CH3:17])([CH3:16])[CH3:15]
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 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 587052255-Amino-3-tert-butyl-pyrazol-1-yl-phenol

生成物 1

HCID 579256593-tert-butyl-1-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)-1H-pyrazol-5-amine収率 134.8%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of intermediate 95a (1.42 g, 6.15 mmol) and triphenyl phosphine (3.22 g, 12.29 mmol) in THF (50 mL), under an atmosphere of argon was treated with 2-(tetrahydro-pyran-2-yloxy)-ethanol (1.25 mL, 9.22 mmol), followed by the dropwise addition of diethyl azodicarboxylate (1.94 mL, 12.29 mmol). The reaction mixture was then stirred at RT for 1 h. Water (0.5 mL) was added and the mixture was concentrated in vacuo. The residue was taken up in EtOAc (8 mL) and cyclohexane was added until triphenylphosphine oxide had precipitated out of solution. This was filtered and the filtrate was concentrated in vacuo. The residue was purified by FCC, using 0-100% EtOAc in cyclohexane to afford the title compound as an orange/brown oil (2.98 g, >100%). LCMS (Method 3): Rt 3.20 min, m/z 360 [MH+].

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. additioncyclohexane was added until triphenylphosphine oxide
  3. customhad precipitated out of solution
  4. filtrationThis was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-5adc8802afe84ed5b463a4974060b1f3
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315503B2

反応ノート

読み込み中…

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