6-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine → (6S*)-6-[(dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine

HRID 2088736Notes

Reaction equation

HRID 2088736 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH2:15])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:3].CCCCCC.C(O)(C)C.C(NCC)C>>[CH3:3][N:2]([CH2:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH2:15])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:1].[CH3:3][N:2]([CH2:4][C@H:5]1[CH2:14][CH2:13][C:12]2[CH:11]=[C:10]([NH2:15])[CH:9]=[CH:8][C:7]=2[CH2:6]1)[CH3:1]

Participants

4

Reactant 2

HCID 219397216-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amineHCID 21973129Hexane isopropanol diethylamine

Product 2

HCID 58289871(6S*)-6-[(dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amineHCID 58289880(6R*)-6-[(dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine

Procedure

6-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine was optically resolved, using CHIRALCEL OD-H (20 mm×250 mm) (hexane/isopropanol/diethylamine=75/25/0.1) to obtain 156 mg of (6R*)-6-[(dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine, and 159 mg of (6S*)-6-[(dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine.

Sources & evidence

ORD record
ord-fcb157dc33884b199e82bfa201aa4624
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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