Ethyl bromoacetate → HCID 86752765, compound

HRID 344044Notes

Reaction equation

[C:1]1([C@@H:7]([NH:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:16]([OH:20])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CS(C)=O>[C:1]1([C@@H:7]([NH:9][CH:10]2[CH2:19][CH2:18][C:17]3[C:16]([O:20][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (6RS)-5,6,7,8-tetrahydro-6-[((1S)-1-phenylethyl)amino]-1-naphthol (267 mg) in dimethylsulfoxide (3 ml) was added dropwise to a stirred suspension of 60% sodium hydride (44 mg, washed with n-hexane) in dimethylsulfoxide (0.5 ml) at room temperature in a nitrogen atmosphere over 15 minutes, and the mixture was stirred at 50° C. for 10 minutes and cooled to room temperature. Ethyl bromoacetate (167 mg) in dimethylsulfoxide (1 ml) was added thereto and the resulting mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed twice with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (dichloromethane-ethanol) over silica gel to afford ethyl [(6RS)-5,6,7,8-tetrahydro-6-[((1S)-1-phenylethyl)amino]-1-naphthyloxy]acetate (243 mg) as a brown oil.

Workup

temperaturecooled to room temperature
stirringthe resulting mixture was stirred at the same temperature for 2 hours
extractionextracted with ethyl acetate
washThe extract was washed twice with brine
dry with materialdried over sodium sulfate
customevaporated in vacuo
customThe residue was chromatographed (dichloromethane-ethanol) over silica gel

Sources & evidence

ORD record: ord-b6e680002c1746b3b35bbc81e1a00c7c
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05863918

Reaction notes

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