Hydroxyamine hydrochloride → HCID 178425580, compound

HRID 1361315Notes

Reaction equation

HRID 1361315 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[CH:28]=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[NH2:31][OH:32]>CO>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:21][CH2:22][C:23]([CH3:27])([CH3:26])[CH2:24][CH2:25]2)[C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:10][C@H:9]1/[CH:28]=[N:31]/[OH:32])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86636644HCID 86636644, compound

Product 1

HCID 178425580HCID 178425580, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4S)-1-Boc-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-2-formylpyrrolidine (312 mg, 0.88 mmol) prepared in Step A in methanol (5 ml) and TEA (0.64 ml, 4.4 mmol) was added hydroxylamine hydrochloride (305 mg, 4.4 mmol), and stirred at rt for 2 h. After the reaction finished, the solution was concentrated in vacuo, and extracted with EtOAC. The organic extracts were washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography (eluent: EtOAc:Hex=1/2) to give the title compound (208 mg, 67%).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. extractionextracted with EtOAC
  3. washThe organic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: EtOAc:Hex=1/2)

Sources & evidence

ORD record
ord-4b8e4a2f2da640bd8361fe7aaad288f8
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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