Dimethylamine → HCID 15453437, compound

HRID 1003286Notes

Reaction equation

HRID 1003286 reaction equation
[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17](OCC)=[O:18])=[CH:10][CH:11]=2)[CH2:6]1.[CH3:29][NH:30][CH3:31]>O1CCCC1>[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([N:30]([CH3:31])[CH3:29])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 15453436HCID 15453436, compound

Product 1

HCID 15453437HCID 15453437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxyphenyl)-ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (250 mg) was dissolved in tetrahydrofuran (5 ml), and dimethylamine (1 ml) was added to the solution under ice-cooling. After reaction in sealed tube at 60° C. for 60 hours, the reaction mixture was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=10/1) gave 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxyphenyl)-ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (189 mg) as an amorphous.

Workup

  1. temperaturecooling
  2. customAfter reaction in sealed tube at 60° C. for 60 hours
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customPurification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-19c5ab398555479ebbb3a15d61def34d
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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