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

HRID 377157Notes

Reaction equation

HRID 377157 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 (x4), 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 (x4)
  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-d85944979ef941daafd119b368eeb4aa
Source dataset
uspto-grants-2000_02
Patent number
US06025350

Reaction notes

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