1,2,3,4-Tetrahydroisoquinoline → HCID 68869800, compound

HRID 2111994Notes

Reaction equation

HRID 2111994 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 68869800HCID 68869800, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Hydroxyphenyl)propionic acid (202 mg, 1.216 mmol) in DMF (3 ml) was cooled in an ice-bath. 1,2,3,4-Tetrahydroisoquinoline (170 mg, 1.276 mmol) was added and then TBTU (410 mg, 1.276 mmol) followed by DIPEA (330 mg, 2.553 mmol). The mixture was stirred at room temperature overnight. Sodium hydrogencarbonate aqueous solution (sat.) was added. The mixture was extracted with ethyl acetate (×2). The extracts were combined and dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 303 mg the desired product, yield 89%.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (×2)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated

Sources & evidence

ORD record
ord-3a96b4a0af4f47c2a35645dd9e7615cc
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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