Diethyl Ether → HCID 66971021, compound

HRID 1361319Notes

Reaction equation

HRID 1361319 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@@H:9]1[C:28](N(OC)C)=[O:29])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:34][Mg]Br.CCOCC>C1COCC1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:26])([CH3:27])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:10][C@@H:9]1[C:28](=[O:29])[CH3:34])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 86636646HCID 86636646, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66971021HCID 66971021, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of BOC (2R,4S)-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-2-{[methoxy(methyl)amino]carbonyl}pyrrolidine (670 mg, 1.44 mmol) prepared in Step B in THF (5 ml) was added methylmagnesium bromide 3M in ether solution (1.2 ml, 3.66 mmol), and the solution was stirred for 3 h. After the reaction finished, the solution was concentrated in vacuo. The residue was diluted with EtOAc, and washed with water and brine. The organic solution was dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc:Hex=3/1) to give the title compound (280 mg, 46%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: EtOAc:Hex=3/1)

Sources & evidence

ORD record
ord-8146a441c23e4a0aabb08a21f53ffa6d
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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