N-bromobutanimide → HCID 67073348, compound

HRID 2253004Notes

Reaction equation

HRID 2253004 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([N:16]1[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>C(#N)C>[C:9]([N:16]1[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][C:23]2[CH:28]=[C:27]([Br:1])[C:26]([O:29][CH3:30])=[CH:25][C:24]=2[O:31][CH3:32])[CH2:17]1)([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67073043HCID 67073043, compound

Product 1

HCID 67073348HCID 67073348, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (29 mg, 0.16 mmol) was added to a solution of N-Boc-(R)-2-(2,4-dimethoxy-benzyl)-morpholine (54 mg, 0.16 mmol) in acetonitrile (6.0 mL). The mixture was shaken for 66 h, concentrated and the residue partitioned between ethyl acetate and water. The organic phase was separated, dried and concentrated to give N-Boc-(R)-2-(5-bromo-2,4-dimethoxy-benzyl)-morpholine which was immediately deprotected using hydrogen chloride (4M in dioxane) in methanol affording example 57 as a brown oil (55 mg, 100%).

Workup

  1. concentrationconcentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa3b1703fd5e467584c096d0c5f6e0b0
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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