N-[(1R,2R)-2-Hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide → N-[(1R)-2-Oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide

HRID 2367342

反応式

HRID 2367342 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12]1)=[O:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:12]1)=[O:10]

参加物

4

反応物 2

HCID 58504652N-[(1R,2R)-2-Hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamideHCID 178418287HCID 178418287、化合物

生成物 1

HCID 58504386N-[(1R)-2-Oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide収率 14.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A suspension of N-[(1R,2R)-2-hydroxycyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide (5.0 g, 15.7 mmol) and pyridinium chlorochromate (PCC) (4.06 g, 18.84 mmol) in CH2Cl2 (79 mL) was stirred at room temperature for 18 hours. The reaction mixture was filtered through a pad of silica gel and washed with EtOAc to get crude product (4.0 g). Purification was carried out on column chromatography (EtOAc—PE, from 2:1 to 2:0) to afford the title compound (0.7 g). LC-MS (ES) m/z=317 [M+H]+.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of silica gel
  2. washwashed with EtOAc
  3. customto get crude product (4.0 g)
  4. customPurification

出典と根拠

ORDレコード
ord-76d085be6b3449a9a8ca2f62c2a275c6
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

関連ノート

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