tert-Butanol → [(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

HRID 1169230ノート

反応式

HRID 1169230 の反応式
[CH:1]([C@@H:9]1[C@H:14](C(O)=O)[CH2:13][CH2:12][CH2:11][O:10]1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:23](=[O:32])[NH:20][C@@H:14]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]1[CH:1]=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH3:45])([CH3:44])[CH3:43]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69748371(2R,3R)-2-Styryl-tetrahydro-pyran-3-carboxylic acid

生成物 1

HCID 69748163[(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester収率 55.5%

反応条件

温度
23 °C

実験手順

To a stirring solution of (2R,3R)-2-styryl-tetrahydro-pyran-3-carboxylic acid (106 mg, 0.456 mmol) in anhydrous tert-butanol (5 mL) under nitrogen in a flame-dried round bottom flask was added sequentially triethylamine (95 μL, 0.684 mmol) and diphenylphosphoryl azide (98 μL, 0.456 mmol). The reaction was warmed to reflux conditions and maintained at reflux for 15 h . The reaction solution was then cooled to 23° C., concentrated, and purified by flash chromatography (SiO2, 30% ethyl acetate in hexanes) to yield the desired carbamate (76.4 mg, 55.5%) as a white solid. MS (ESI), m+/z: (M+H)+=304.3.

後処理

  1. temperatureThe reaction was warmed
  2. temperatureto reflux conditions
  3. temperaturemaintained
  4. temperatureat reflux for 15 h
  5. concentrationconcentrated
  6. custompurified by flash chromatography (SiO2, 30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c03e9aaa0c244fe4938096d9b4b84cb6
出典データセット
uspto-grants-2003_09
特許番号
US06627629B2

反応ノート

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