Sodium cyanoborohydride → HCID 66679365, compound

HRID 1019674Notes

Reaction equation

HRID 1019674 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=O)[CH2:9]2)=[CH:4][C:3]=1[F:13].[BH3-]C#[N:16].[Na+]>CO>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([NH2:16])[CH2:9]2)=[CH:4][C:3]=1[F:13]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 66679343HCID 66679343, compound2×

Product 1

HCID 66679365HCID 66679365, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Bromo-6-fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine XVI was prepared from commercial available 7-bromo-6-fluoro-3,4-dihydro-1H-naphthalen-2-one XV. To a stirred solution of XV (0.10 g, 0.41 mmol) in 3 mL of MeOH was added NH4OAc, followed by NaCNBH3 (0.018 g) in one portion at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 h. Removal of solvent under vacuum gave the crude product, which was partitioned between 2N Na2CO3 and CH2Cl2. The organic layer was separated and dried over MgSO4. The solvent was removed under vacuum and the so-obtained crude product was dissolved in 2 mL of CH2Cl2. To this solution was added TEA (0.12 mL) and (Boc)2O (90 mg, 0.41 mmol). The reaction mixture was stirred at rt overnight. Removal of the solvent under vacuum gave the crude product, which was purified by column to give the pure product XVII (119 mg, 84% over 2 steps). MS: calc'd (MH+) 344, exp (MH+) 344.

Workup

  1. customRemoval of solvent under vacuum
  2. customgave the crude product, which

Sources & evidence

ORD record
ord-54f28321c8834d6181089fa34250afb5
Source dataset
uspto-grants-2014_05
Patent number
US08716285B2

Reaction notes

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