Sodium Hydroxide → HCID 18963909, compound

HRID 257072Notes

Reaction equation

HRID 257072 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH:27]=[N:28][OH:29])[CH:21]=4)[C:16]3=[O:30])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[OH-].[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:26][CH2:27][NH:28][OH:29])[CH:21]=4)[C:16]3=[O:30])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 73473594HCID 73473594, compound

Product 1

HCID 18963909HCID 18963909, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the above oxime (9 g, 22.28 mmol) in glacial acetic acid (50 ml) and CH2Cl2 (75 ml) is added sodium cyanoborohydride (1.7 g). The solution is stirred for 45 minutes at room temperature and subsequently diluted with H2O (200 ml). The resulting mixture is then neutralized with 5N NaOH and solid NaHCO3. The reaction mixture is extracted with EtOAc (2×200 ml) and the combined organic layers washed with saturated NaCl solution, dried over MgSO4, and concentrated in vacuo to yield 2-(4'-fluoro-4-biphenylylmethyl)-6-[2-(N-hydroxyamino)ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. extractionThe reaction mixture is extracted with EtOAc (2×200 ml)
  2. washthe combined organic layers washed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a5a2627f5ce42c1b9ee4fd59e9eb73f
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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