Ammonium Chloride → N-((1R)-1-benzyl-2-hydroxypent-4-enyl)-N-methylcarbamic acid tert-butylester

HRID 1701052Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[N:7]([C@@H:9]([CH:17]=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([Mg]Br)[CH:21]=[CH2:22].[Cl-].[NH4+]>CCOCC.O>[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:17]([OH:18])[CH2:22][CH:21]=[CH2:20])[CH3:8])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

N-((1R)-1-Formyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester (6.0 g, 20.0 mmol) was dissolved in ether (150 mL). The solution was cooled to −78° C. and allylmagnesium bromide (22 mL of a 1.0 M solution in ether, 22 mmol) was added dropwise. After addition, the solution was warmed to room temp. It was given onto 10% ammonium chloride solution in water (200 mL). The phases were separated. The aqueous phase was extracted with ethyl acetate (3×50 mL). The organic layers were combined and washed with satd. sodium hydrogencarbonate solution (100 mL) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (260 g) with ethyl acetate/heptane 1:1 to give 4.00 g of N-((1R)-1-benzyl-2-hydroxypent-4-enyl)-N-methylcarbamic acid tert-butylester.

Workup

additionAfter addition
temperaturethe solution was warmed to room temp
customThe phases were separated
extractionThe aqueous phase was extracted with ethyl acetate (3×50 mL)
washwashed with satd
dry with materialsodium hydrogencarbonate solution (100 mL) and dried over magnesium sulfate
customThe solvent was removed in vacuo
customThe crude product was purified by flash chromatography on silica (260 g) with ethyl acetate/heptane 1:1

Sources & evidence

ORD record: ord-ff39b596397a4c8c9b0dc17d6968d753
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350767B1

Reaction notes

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