HCID 178464020, compound → HCID 178464460, compound

HRID 25587Notes

Reaction equation

HRID 25587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:27])[N:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]#[C:19][CH2:20][N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][OH:24])[CH2:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9](=[O:27])[N:10]([C@H:12]2[CH2:13][CH2:14][C@H:15]([CH2:18][CH2:19][CH2:20][N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][OH:24])[CH2:16][CH2:17]2)[CH3:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 178464020HCID 178464020, compound

Product 1

HCID 178464460HCID 178464460, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 65 mg (0.165 mmol) of trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-prop-1-ynyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester in 5 ml MeOH and 7 mg Pt/C 10% was hydrogenated (1 atm) for 16 h. The reaction was filtered (Celite) and evaporated. Flash column chromatography on silica gel with CH2Cl2/MeOH (9:1) gave 21 mg (32%) of trans-(4-{3-[Ethyl-(2-hydroxy-ethyl)-amino]-propyl}-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 397 (MH+, 1Cl).

Workup

  1. customfor 16 h
  2. filtrationThe reaction was filtered (Celite)
  3. customevaporated

Sources & evidence

ORD record
ord-1c95c33d84ec4393a59ed7975d903883
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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