Methanol → 2-Propanesulfinamide, 2-methyl-N-[(1S)-1,2,3,4-tetrahydro-5-(2,2,2-trifluoroethoxy)-1-naphthalenyl]-, [S(R)]-
Reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[CH3:15][C:16]([S@:19](/[N:21]=[C:22]1/[CH2:23][CH2:24][CH2:25][C:26]2[C:31]/1=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH2:33][C:34]([F:37])([F:36])[F:35])=[O:20])([CH3:18])[CH3:17].CO>C1COCC1.[Cl-].[Na+].O>[CH3:18][C:16]([S@:19]([NH:21][C@@H:22]1[C:31]2[C:26](=[C:27]([O:32][CH2:33][C:34]([F:35])([F:36])[F:37])[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:20])([CH3:15])[CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of L-Selectride (3.90 mL, 3.90 mmol) in THF (1 mL) was added Intermediate 13A (0.45 g, 1.3 mmol) in THF (1 mL) at −50° C. The reaction mixture was warmed up to rt until the reduction was complete. To the reaction mixture was added MeOH (2 mL) and brine (2 mL). The resulting reaction mixture was stirred for 5 minutes, filtered, and the filtrate was concentrated in vacuo. The crude product was dissolved in a small amount of DCM and loaded on a 4 g silica gel cartridge eluting from 0 to 100% EtOAc in hexanes over 15 minutes to give Intermediate 13B (196 mg, 0.561 mmol, 43.1% yield). LCMS=2.09 min [M+1]=350 (Method B).
Workup
- customThe resulting reaction mixture
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
- dissolutionThe crude product was dissolved in a small amount of DCM
- washeluting from 0 to 100% EtOAc in hexanes over 15 minutes
Sources & evidence
- ORD record
- ord-c76a0d2ebb1149f6a4eba20ff78349e1
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199946B2
Reaction notes
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