Benzylamine → HCID 86755475, compound

HRID 1421896Notes

Reaction equation

HRID 1421896 reaction equation
CO[C:3](=[O:16])[CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][C:6]1=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].[Na]>CO.O1CCCC1.C(O)(=O)C>[CH2:17]([N:24]1[C@@H:6]2[C@@H:5]([CH2:14][C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:7]2)[CH2:4][C:3]1=[O:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 5003444Sodium cyanoborohydrideHCID 5360545SodiumHCID 14090224HCID 14090224, compound

Product 1

HCID 86755475HCID 86755475, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (12.5 ml) was added to a stirred mixture of 2-oxo-1,2,3,4-tetrahydronaphthalene-3-acetic acid methyl ester (3.62 g, 17 mmol), and benzylamine (7.2 ml, 66 mmol) in a 1:1 mixture of tetrahydrofuran and methanol (120 ml) at 0° C. under argon. After 0.5 h, sodium cyanoborohydride (2.09 g, 33 mmol) was added and the resultant mixture stirred at room temperature. After 16 h, aqueous 10% sodium hdyroxide was added and the solvent evaporated in vacuo. The residue was partitioned between water (100 ml) and dichloromethane (2×200 ml). The combined extracts were washed with water (100 ml), brine (100 ml), then dried (Na2SO4) and evaporated in vacuo to give a brown solid (4.38 g). Chromatography on silica using 0-5% methanol-ethyl acetate gradient elution afforded the title compound as a yellow solid (1.75 g, 38%).

Workup

  1. waitAfter 16 h
  2. customthe solvent evaporated in vacuo
  3. customThe residue was partitioned between water (100 ml) and dichloromethane (2×200 ml)
  4. washThe combined extracts were washed with water (100 ml), brine (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-874de03fa9ab44a19f8163331e253d88
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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