Water → N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine

HRID 2252975Notes

Reaction equation

HRID 2252975 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:22]N1C(=O)CCC1=O.O>CN(C)C=O>[C:1]([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([Br:22])[CH:16]=2)[CH2:9]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58689710N-BOC-(R)-2-(4-hydroxybenzyl)morpholine

Product 1

HCID 67073493N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of intermediate (b), N-BOC-(R)-2-(4-hydroxybenzyl)morpholine (1.0 g, 3.41 mmol) in anhydrous N,N-dimethyl formamide (10 mL), under at atmosphere of nitrogen at room temperature was added N-bromosuccinimide (0.63 g, 3.58 mmol). The resulting solution was stirred at room temperature for 2 hrs and then poured into water (50 mL) and extracted with ethyl acetate (70 mL×2). Combined organic layers were washed with water (2×50 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The material was concentrated onto sodium sulfate and purified by column chromatography (silica; 17% ethyl acetate/isohexane) to yield the desired intermediate (a), N-BOC-(R)-2-(3-bromo-4-hydroxybenzyl)morpholine, as a white solid (0.89 g).

Workup

  1. extractionextracted with ethyl acetate (70 mL×2)
  2. washCombined organic layers were washed with water (2×50 mL), brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationThe material was concentrated onto sodium sulfate
  7. custompurified by column chromatography (silica; 17% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-5118163905384bf98750c4a38bd55190
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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