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Cesium carbonate → (R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate

HRID 2277042
ノート
印刷プレビュー

反応式

HRID 2277042 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].CS([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)(=O)=O.[OH:19][C@@H:20]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33](O)[CH:32]=1)[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[NH4+].[Cl-]>CN(C=O)C>[OH:19][C@@H:20]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:36]=1)[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

生成物 1

HCID 90448349(R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Cs2CO3 (2.34 g, 7.18 mmol) was added to a solution of (tetrahydro-2H-pyran-4-yl)methyl methanesulfonate (1.05 g, 5.41 mmol) and Intermediate I (1.13 g, 4.23 mmol) in anhydrous DMF (11 mL) and the reaction mixture was heated at +70° C. under Ar for 22 hrs. Aqueous NH4Cl (25%) was added and the reaction mixture was extracted with MTBE twice. Combined organic layers were washed with brine, concentrated under reduced pressure. Purification by flash chromatography (25%-100% EtOAc-hexanes gradient) gave (R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate as a colorless oil. Yield (0.47 g, 30%); 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, J=8.0 Hz, 1H), 6.85-6.84 (m, 2H), 6.76-6.74 (m, 2H), 5.15 (d, J=4.4 Hz, 1H), 4.49 (q, J=4.4 Hz, 1H), 3.88-3.84 (m, 2H), 3.79 (d, J=6.4 Hz, 2H), 2.94 (q, J=6.4 Hz, 2H), 1.70-1.62 (m, 4H), 1.38-1.26 (m, 11H).

後処理

  1. temperaturethe reaction mixture was heated at +70° C. under Ar for 22 hrs
  2. extractionthe reaction mixture was extracted with MTBE twice
  3. washCombined organic layers were washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (25%-100% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-5cd105993c4c4d4692882a051c192864
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133154B2

反応ノート

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