Triethylamine → (6S)-6-[Benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate
Reaction equation
[O:1](S(C(F)(F)F)(=O)=O)[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH2:16]([N:23]([CH3:35])[C@H:24]1[CH2:33][CH2:32][C:31]2[C:30](O)=[CH:29][CH:28]=[CH:27][C:26]=2[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC.[O-]S(C(F)(F)F)(=O)=O>C(Cl)Cl.CO.C(Cl)Cl>[F:6][C:5]([F:8])([F:7])[S:2]([O:1][C:30]1[C:31]2[CH2:32][CH2:33][C@H:24]([N:23]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:35])[CH2:25][C:26]=2[CH:27]=[CH:28][CH:29]=1)(=[O:4])=[O:3]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Tf2O (3.6 mL, 21.309 mmol) was dropwise added to a −78° C. cooled solution of (6S)-6-[benzyl(methyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol (5.30 g, 19.822 mmol) and Et3N (6 mL, 43.04 mmol) in CH2Cl2 (100 mL). Addition time: ca. 5 min. The reaction was completed after 15 min at low temperature (TLC analysis). The reaction mixture was poured into CH2Cl2 (250 mL) and washed with H2O (200 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was flash chromatographed on silica gel (1-2-3% MeOH/CH2Cl2), to furnish two batches of product: 5.78 g of pure triflate, and 1.90 g of product slightly impure (TLC analysis) (Rf=0.8 (10% MeOH/CH2Cl2), off-white solid, 73% and 24% yield).
Workup
- additionAddition time
- customca. 5 min
- washwashed with H2O (200 mL)
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customchromatographed on silica gel (1-2-3% MeOH/CH2Cl2)
- customto furnish two batches of product
Sources & evidence
- ORD record
- ord-23889cd77efe427dacf8a06f00d2eb72
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097641B2
Reaction notes
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