Methylamine → (1S,2S)-6-fluoro-1-isopropyl-2-(2-methylamino-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol

HRID 2090568Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][CH2:17]OS(C1C=CC(C)=CC=1)(=O)=O)([OH:15])[CH2:6][CH2:5]2.[CH3:29][NH2:30]>CCO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C@H:8]([CH:12]([CH3:14])[CH3:13])[C@:7]([CH2:16][CH2:17][NH:30][CH3:29])([OH:15])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 40 °C

Procedure

8 g of toluene-4-sulfonic acid 2-((1S,2S)-6-fluoro-2-hydroxy-1-isopropyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-ethyl ester were dissolved in a 8 M solution of MeNH2 in EtOH (100 mL). The mixture was stirred overnight in at 40° C., diluted with DCM and washed with sat.-NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated to give 5.29 g of (1S,2S)-6-fluoro-1-isopropyl-2-(2-methylamino-ethyl)-1,2,3,4-tetrahydro-naphthalen-2-ol as beige solid.

Workup

washwashed with sat.-NaHCO3
dry with materialThe organic phase was dried over anh. Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-3ea67aad68214b67ad40170b07a7f341
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436205B2

Reaction notes

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