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Triphenylphosphine → 2-[3-((R)-2-Benzyloxy-1-methyl-ethoxy)-phenyl]-5-tert-butyl-2H-pyrazol-3-ylamine

HRID 2282720
ノート
印刷プレビュー

反応式

HRID 2282720 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.[CH2:37]([O:44][CH2:45][C@@H:46]([OH:48])[CH3:47])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CO.O>[CH2:37]([O:44][CH2:45][C@@H:46]([CH3:47])[O:48][C:9]1[CH:8]=[C:7]([N:6]2[C:2]([NH2:1])=[CH:3][C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])=[N:5]2)[CH:12]=[CH:11][CH:10]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
参加物反応条件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 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13197475(2S)-1-(benzyloxy)propan-2-olHCID 587052255-Amino-3-tert-butyl-pyrazol-1-yl-phenol

生成物 1

HCID 866872762-[3-((R)-2-Benzyloxy-1-methyl-ethoxy)-phenyl]-5-tert-butyl-2H-pyrazol-3-ylamine収率 45%

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 962Water溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of Intermediate 95a (0.50 g, 2.2 mmol) in dry THF (17 mL) was treated with triphenylphosphine (1.13 g, 4.32 mmol) and (S)-(+)-1-Benzyloxy-2-propanol (0.52 mL, 3.24 mmol). The mixture was cooled to 0° C. then diisopropylazodicarboxylate (0.85 mL, 4.32 mmol) was added dropwise. After stirring at ambient temperature for 1.75 h the mixture was treated with water (0.2 mL) then applied to a pre-conditioned (with MeOH) SCX-2 cartridge. The cartridge was eluted with MeOH then 2N NH3 in MeOH. The product containing fractions were combined and concentrated in vacuo to a viscous brown oil. The oil was purified by FCC, using 0-30% EtOAc in cyclohexane, to give the title compound as a golden oil (0.37 g, 45%). LCMS (Method 3): Rt 3.71 min, m/z 380.3 [MH+].

後処理

  1. washThe cartridge was eluted with MeOH
  2. additionThe product containing fractions
  3. concentrationconcentrated in vacuo to a viscous brown oil
  4. customThe oil was purified by FCC

出典と根拠

ORDレコード
ord-6a25f3b9d3714ca196ab056d2fb43289
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139584B2

反応ノート

読み込み中…

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