(1R,2S)-(+)-cis-1-Amino-2-indanol → (S)-Tenatoprazole

HRID 490961Notes

Reaction equation

HRID 490961 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([S:12][CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17]([CH3:23])=[CH:16][N:15]=3)[NH:11][C:6]2=[CH:5][CH:4]=1.N[C@@H]1C2C(=CC=CC=2)C[C@@H]1[OH:34].[O-]O.C1(C(C)C)C=CC=CC=1>CN(C=O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:23][C:17]1[C:18]([O:21][CH3:22])=[C:19]([CH3:20])[C:14]([CH2:13][S@@:12]([C:10]2[NH:11][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:8][C:7]=3[N:9]=2)=[O:34])=[N:15][CH:16]=1

Participants

6

Reactant 3

HCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 98404895-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-imidazo[4,5b]pyridineHCID 53627471Cumen hydroperoxide

Product 1

HCID 11552393(S)-Tenatoprazole

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
22 °C

Procedure

5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]thio]imidazo[4,5-b]pyridine (100 mg, 0.303 mmol) is solubilised in anhydrous DMF (0.65 mL). Titanium isopropoxide (IV) (22 μl, 0.076 mmol) and (1R,2S)-(+)-1-amino-2-indanol (22.8 mg, 0.151 mmol) in anhydrous DMF are added under stirring at 22° C., followed by cumene hydroperoxide (80%, 65 μL, 0.352 mmol).

Sources & evidence

ORD record
ord-1b119dbbb71e4537983dbfb12a1cadc0
Source dataset
uspto-grants-2009_05
Patent number
US07528251B2

Reaction notes

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