Tetrahydrofuran → Benzyl [(1S)-1-(4-hydroxyphenyl)ethyl]carbamate

HRID 330765Notes

Reaction equation

HRID 330765 reaction equation
Br.[NH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4].C1COCC1.C([O-])(O)=O.[Na+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>O>[OH:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:3]([NH:2][C:23](=[O:24])[O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:4])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 75273665HCID 75273665, compound

Product 1

HCID 59899326Benzyl [(1S)-1-(4-hydroxyphenyl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.00 g (22.9 mmol) 4-(1-amino-ethyl)-phenol hydrobromide are added to 10 mL THF and 10 mL H2O before 13.5 g (160 mmol) NaHCO3 are added. Then 3.60 mL (25.2 mmol) benzyl chloroformate are added dropwise and the reaction mixture is stirred at r.t. for 3 h. Afterwards the reaction mixture is quenched by the addition of water and is set to a gentle acidic pH value using citric acid (10% in water). Then the product is extracted with EtOAc, the combined organic layers are dried over MgSO4, filtered and the solvent is removed in vacuo. The crude product is purified by flash chromatography (silica gel, PE/EtOAc).

Workup

  1. additionare added
  2. customAfterwards the reaction mixture is quenched by the addition of water
  3. extractionThen the product is extracted with EtOAc
  4. dry with materialthe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe crude product is purified by flash chromatography (silica gel, PE/EtOAc)

Sources & evidence

ORD record
ord-da3e75460dd447ff94397858715c3e48
Source dataset
uspto-grants-2014_11
Patent number
US08877741B2

Reaction notes

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