Tyramine → HCID 69099606, compound

HRID 2251569Notes

Reaction equation

HRID 2251569 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.COC(OC)OC.[BH4-].[Na+]>CO.C1COCC1>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:16]=[CH:15][C:12]([CH2:13][NH:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=4)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 5610TyramineHCID 9005Trimethyl orthoformateHCID 4311764Sodium borohydrideHCID 596432084-(2-Cyclopropyl-1,3-oxazol-4-yl)benzaldehyde

Product 1

HCID 69099606HCID 69099606, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-cyclopropyl-1,3-oxazol-4-yl)benzaldehyde (0.318 g, 1.49 mmol) in MeOH (5 ml) was added tyramine (0.215 g, 1.57 mmol) and trimethylorthoformate (1.2 mL, 10.97 mmol). The resulting solid was redissolved in THF (3 ml) and allowed to stir for 12 h. Sodium borohydride (0.15 g, 3.94 mmol) was added and the mixture was stirred an additional 2 h. The reaction mixture was concentrated and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried with MgSO4, and concentrated in vacuo. The crude material was purified by flash chromatography (MeOH/CH2Cl2, 5:95 to 10:90) to yield 4-(2-{[4-(2-cyclopropyl-1,3-oxazol-4-yl)benzyl]amino}ethyl)phenol as a white solid (0.43 g, 85%).

Workup

  1. stirringthe mixture was stirred an additional 2 h
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (MeOH/CH2Cl2, 5:95 to 10:90)

Sources & evidence

ORD record
ord-bf358893abcb487eb7692e8fa8c29dbc
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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