Ozone → [(2R,3R)-2-formyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

HRID 497483ノート

反応式

HRID 497483 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]1[CH:14]=CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].[O:23]=[O+][O-]>CO>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@H:9]1[CH:14]=[O:23])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 24823OzoneHCID 69748163[(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 59094967[(2R,3R)-2-formyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester収率 98%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
23 °C

実験手順

Through a stirring solution of [(2R,3R)-2-styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (27 mg, 0.089 mmol) in methanol (2 mL) at −78° C. was bubbled ozone until the reaction solution was blue in color. Excess triphenylphosine (500 mg) was added, and the reaction was allowed to warm to 23° C. The resulting mixture was concentrated and purified by flash chromatography (SiO2, 7-40% ethyl acetate in hexanes) to give the desired aldehyde (20 mg, 98%) as a pale yellow oil. MS (APCI), m+/z: (M+H)+=230.

後処理

  1. additionExcess triphenylphosine (500 mg) was added
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by flash chromatography (SiO2, 7-40% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c740780a48b740b2a1b1a90616b60dcf
出典データセット
uspto-grants-2005_09
特許番号
US06949546B2

反応ノート

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