Sodium Phosphate, Dibasic → HCID 59396535, compound

HRID 2383065Notes

Reaction equation

HRID 2383065 reaction equation
C([Li])CCC.[CH3:6][O:7][CH2:8][CH:9]1[C:18]2[C:13](=[C:14]([CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](O[C@@H]2C[C@H](C)CC[C@H]2C(C)C)=[O:28])=[CH:23][CH:22]=1.P(O)([O-])([O-])=O.[Na+].[Na+]>CCCCCC.C1COCC1>[CH3:6][O:7][CH2:8][C@H:9]1[C:18]2[C:13](=[C:14]([CH3:19])[CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][N:10]1[S@@:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:20])=[CH:22][CH:23]=1)=[O:28]

Participants

7

Reactant 4

HCID 24203Sodium Phosphate, DibasicHCID 10968417HCID 10968417, compoundHCID 67537337HCID 67537337, compoundHCID 178418339Butyllithium

Product 1

HCID 59396535HCID 59396535, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1.55 M n-butyllithium in hexane (10.94 mL) was added with stirring to a solution of 1-(methoxymethyl)-5-methyl-1,2,3,4-tetrahydroisoquinoline (3.07 g) in THF (60 mL) under an argon atmosphere, over about 8 minutes, at −70° C. or below, followed by further stirring for 30 minutes. To the reaction mixture was added with stirring a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-methylbenzenesulfinate (3.375 g) in THF (25 ml) over 5 minutes at −70° C. or below, followed by further stirring for 1 hour. Thereafter, saturated disodium phosphate was added to the mixture at the same temperature and the temperature was increased to room temperature. The mixture was extracted with ether. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate and then the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (hexane:EtOAc) to obtain (1R)-1-(methoxymethy)-5-methyl-2-[(R)-(4-methylphenyl)sulfinyl]-1,2,3,4-tetrahydroisoquinoline (2.144 g) (Rf value=0.14).

Workup

  1. additionTo the reaction mixture was added
  2. stirringby further stirring for 1 hour
  3. extractionThe mixture was extracted with ether
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:EtOAc)

Sources & evidence

ORD record
ord-6762af7627e74ccfbdd70b94fc62e203
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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