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

HRID 2367342

반응식

HRID 2367342 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-76d085be6b3449a9a8ca2f62c2a275c6
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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