Pyridine → HCID 178476335, compound

HRID 1743786Notes

Reaction equation

HRID 1743786 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[C:19](OC(=O)C)(=[O:21])[CH3:20].N1C=CC=CC=1>ClCCl.CCOCC>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][O:17][C:19](=[O:21])[CH3:20])[CH2:12][CH2:11]1)=[O:18])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178453494HCID 178453494, compound

Product 1

HCID 178476335HCID 178476335, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 27.9 g (86.7 mmol) trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester, 41 ml (434 mmol) acetic anhydride and 35 ml (434 mmol) of pyridine in 140 ml of dichloromethane was stirred at room temperature for 16 hours. The reaction-mixture was then taken up in Et2O and washed with 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water. Then, the Et2O-phase was dried over magnesium sulfate and concentrated to yield 26.0 g crude trans-acetic acid 4-(2-tert-butoxycarbonylamino-ethyl)-cyclohexylmethyl ester as colorless viscous oil, MS: 200 [(M-(tert-butoxycarbonyl))H+].

Workup

  1. washwashed with 1N hydrogen chloride solution, sodium hydrogen carbonate solution and water
  2. dry with materialThen, the Et2O-phase was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-da6aa925b69b435781135654b89586ae
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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