Sodium borohydride → 5-({[6-(Bicyclo[2.2.1]hept-5-en-2-yl)hexyl]amino}methyl)quinolin-8-ol

HRID 2213701Notes

Reaction equation

HRID 2213701 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]=[CH:15][C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2.[BH4-].[Na+]>CO.O>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[N:21]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 135744156HCID 135744156, compound

Product 1

HCID 210516855-({[6-(Bicyclo[2.2.1]hept-5-en-2-yl)hexyl]amino}methyl)quinolin-8-olYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Imine 7 was dissolved in 50 mL of dry methanol and 1 equivalent of NaBH4 (0.136 g, 0.0036 mol) was added in small increments. After the addition was complete, the solution was allowed to stir for 10 minutes at room temperature. The solution was diluted with water and extracted three times with 20 mL of methylene chloride. The combined organic layers were washed with water, NaHCO3, brine, and dried over Na2SO4. The solvent was removed under reduced pressure to yield a brown liquid. Purification by column chromatography (silica gel, 4:1 hexanes/ethyl acetate, then pure ethyl acetate, then 5% methanol in ethyl acetate) gave the product as a pale yellow solid (0.658 g, 50%). 1H NMR (300 MHz, CDCl3) δ8.75 (1H, dd, J=1.09, 4.39); 8.51 (1H, dd, J=1.09, 8.24); 7.46 (1H, dd, J=4.39, 8.24); 7.38 (1H, d, J=7.69); 7.08 (1H, d, J=7.69); 6.11 (1H endo, dd, J=2.74, 5.49); 6.06–5.99 (2H exo, m); 5.90 (1H endo, dd, J=2.74, 5.49); 4.10 (1H, s); 2.73 (2H, s); 2.71 (2H, t, J=7.14); 1.99–1.02 (12H, m); 0.49–0.43 (1H, m). 13C NMR (75 MHz, CDCl3) δ151.8; 147.6; 137.0; 136.3; 133.4; 132.6; 128.0; 127.4; 126.8; 121.8; 109.2; 51.2; 50.0; 49.7; 45.5; 42.7; 38.9; 34.9; 32.6; 30.2; 29.9; 28.8; 27.5. Anal. Calcd for C23H30N2O: C, 78.88; H, 8.63; N, 8.00. Found C: 78.79, H: 8.72, N: 8.00.

Workup

  1. additionAfter the addition
  2. extractionextracted three times with 20 mL of methylene chloride
  3. washThe combined organic layers were washed with water, NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed under reduced pressure
  6. customto yield a brown liquid
  7. customPurification by column chromatography (silica gel, 4:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-59c78bf734024f748414a13f6afab08e
Source dataset
uspto-grants-2006_09
Patent number
US07105617B2

Reaction notes

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