Pyridine → HCID 178476335, compound

HRID 1063639Notes

Reaction equation

HRID 1063639 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>C(Cl)Cl.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) of trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-carbamic acid tert-butyl ester, 41 mL (434 mmol, 5 eq) of acetic anhydride and 35 mL (434 mmol, 5 eq) of pyridine in 140 mL of CH2Cl2 was stirred at RT for 16 h. The reaction mixture was then taken up in ether and washed with 1M HCl, sodium hydrogen carbonate solution and water. Then, the ether-phase was dried over MgSO4 and concentrated to yield 26.0 g of 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 1M HCl, sodium hydrogen carbonate solution and water
  2. dry with materialThen, the ether-phase was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-658e5ab96095475fa3cf9eb0aab54452
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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