Diethyl Ether → cis-1-(4-benzyloxyphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indane

HRID 965221Notes

Reaction equation

HRID 965221 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:34]=[CH:33][C:14]([O:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@@H:17]2[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.IC.[CH2:37](OCC)C>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:34]=[CH:33][C:14]([O:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@@H:17]2[N:25]([CH3:37])[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18661292(+/-)cis-1-(4Benzyloxyphenoxy)-2-tert-butoxycarbonylaminoindane

Product 1

HCID 18661291cis-1-(4-benzyloxyphenoxy)-2-(N-methyl-N-tert-butoxycarbonylamino)indane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The title compound was prepared in a similar manner to Preparation 19 from sodium hydride (80% disp. in oil, 83 mg, 2.76 mmol) in dry N,N-dimethylformamide (5 ml), (±)cis-1-(4-benzyloxy phenoxy)-2-tert-butoxycarbonylaminoindane (1 g, 2.3 mmol) in N,N-dimethylformamide (5 ml) and iodomethane (175 μl, 2.76 mmol). Column chromatography on silica gel eluting with a gradient of 10-15% diethyl ether in hexanes afforded the title compound (968 mg) as a colourless oil.

Sources & evidence

ORD record
ord-48be4b8bc12240ff9c1a5266525a0c4c
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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