4-Methylmorpholine → N-t-Butoxycarbonyl-2-Hydroxy-5-Chlorobenzylamine

HRID 361365Notes

Reaction equation

HRID 361365 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][NH2:5].S(=O)(=O)(O)[O-].[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.CN1CCOCC1>CN(C=O)C>[C:20]([O:19][C:17]([NH:5][CH2:4][C:3]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:2]=1[OH:1])=[O:16])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 61778Sulfate, hydrogenHCID 90495Di-tert-butyl dicarbonateHCID 2308442-(Aminomethyl)-4-chlorophenol

Product 1

HCID 11311441N-t-Butoxycarbonyl-2-Hydroxy-5-Chlorobenzylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-5-chlorobenzylamine (1.22 g, 4.77 mmol assuming the bisulfate salt), (BOC)2O (1.56 g, 7.16 mmol) and N-methylmorpholine (1.05 ml, 9.54 mmol) in DMF (10 ml) was stirred for 5 h at r.t. The reaction was partitioned between water and ethyl acetate and the organic layer was washed with 5% KHSO4 solution (2 times), sodium hydrogen carbonate solution and brine, dried (Na2SO4) and evaporated in vacuo to a solid. The crude product was recrystallized from ethyl acetate/hexanes (1:5, 12 ml) to give the title compound:

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with 5% KHSO4 solution (2 times), sodium hydrogen carbonate solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo to a solid
  5. customThe crude product was recrystallized from ethyl acetate/hexanes (1:5, 12 ml)

Sources & evidence

ORD record
ord-e96e2b07aa7f44d18e061ff6a4f9d04f
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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