Water → HCID 59396310, compound

HRID 2383049Notes

Reaction equation

HRID 2383049 reaction equation
C[Li].[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)C1C(OCC)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:25](=O)=O.[CH3:28][C:29]([CH3:31])=[O:30].O>C(OCC)C.C1COCC1>[CH2:3]([N:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:28]1[C:29]([OH:30])([CH3:25])[CH3:31])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 18522661Acetone cardice2×HCID 59396192Ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylateHCID 178418348HCID 178418348, compound2×

Product 1

HCID 59396310HCID 59396310, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

In a dry ice-acetone bath under an argon atmosphere, a solution of 1.0 M methyllithium in diethyl ether (16.2 mL) was added dropwise to a solution of ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (1.99 g) in THF (20 mL) over 15 minutes. The reaction liquid was stirred in a dry ice-acetone bath for 0.5 hours and then further stirred in an ice bath for 1 hour. The reaction liquid was cooled again in the dry ice-acetone bath, and a solution of 1.04 M methyllithium in diethyl ether (3.24 mL) was added thereto. The reaction liquid was stirred in the dry ice-acetone bath for 0.5 hours and then stirred in the ice bath for 1 hour. Water was added to the reaction liquid, followed by extraction with EtOAc. The extract was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-(2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-ol (1.27 g).

Workup

  1. customThe reaction liquid
  2. stirringfurther stirred in an ice bath for 1 hour
  3. customThe reaction liquid
  4. customThe reaction liquid
  5. extractionfollowed by extraction with EtOAc
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

Sources & evidence

ORD record
ord-d19eb893e32247168961ea72dbcb3cac
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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