Diethyl Ether → 5-(N-(carbobenzyloxy)amino)-5-(2-methoxyphenyl)-1-pentene

HRID 379514Notes

Reaction equation

HRID 379514 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH2:3][CH2:4][CH:5]=[CH2:6].[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][O:22][C:23](Cl)=[O:24])=[CH:17][CH:16]=1.CCOCC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:23]([NH:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[CH2:3][CH2:4][CH:5]=[CH2:6])([O:22][CH2:21][C:18]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1)=[O:24]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 158847235-Amino-5-(2-methoxyphenyl)-1-pentene

Product 1

HCID 158847245-(N-(carbobenzyloxy)amino)-5-(2-methoxyphenyl)-1-penteneYield 66.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of crude 5-amino-5-(2-methoxyphenyl)-1-pentene (1.63 g) in CH2Cl2 (10 mL) at 0° C. was added DMAP (1.15 g, 9.38 mmol) followed by Cbz-Cl (1.34 mL, 9.38 mmol) and the resulting solution was stirred at room temperature overnight. Ether was added, the aqueous layer was extracted with diethyl ether (×4), and the combined organic layers was washed with brine, dried over MgSO4 and evaporated in vacuo. The crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes) to provide the title compound as a white solid (1.84 g). 1H NMR (CDCl3, 400 MHz) δ: 3.82 (3H, s, OMe), 2.0 (4H, m).

Workup

  1. extractionthe aqueous layer was extracted with diethyl ether (×4)
  2. washthe combined organic layers was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes)

Sources & evidence

ORD record
ord-3289f277c5694209a79558140dedfcf9
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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