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

HRID 2367342

Reaction equation

HRID 2367342 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-76d085be6b3449a9a8ca2f62c2a275c6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Linked notes

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