Methylamine → HCID 86591331, compound

HRID 895318Notes

Reaction equation

HRID 895318 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([CH2:9][C:10]1[C:11]2[C:16]([C:17]([CH:24]=O)=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:27][NH2:28].[BH4-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6](=[O:26])[N:7]([CH3:8])[CH2:9][C:10]1[C:11]2[C:16]([C:17]([CH2:24][NH:28][CH3:27])=[C:18]3[C:23]=1[CH:22]=[CH:21][CH:20]=[CH:19]3)=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86591330HCID 86591330, compound

Product 1

HCID 86591331HCID 86591331, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 4 (2.29 g, 6.56 mmol) was dissolved in the mixture of THF (50 mL) and MeOH (50 mL). To this solution was added the aqueous solution of methylamine (40%, wt, 20 mL), the reaction mixture was stirred at room temperature under nitrogen for 12 h. Sodium borohydride (1.00 g, 26.3 mmol) was added, and stirred for 30 min. After removal of the solvent in vacuo, the resulting residue was dissolved in ethyl acetate (100 mL), washed with water (3×50 mL), and dried over MgSO4. Solvent evaporation gave a crude product, which was purified on a silica gel column, eluting with MeOH/CH2Cl2 (1/2), giving compound 5 as a yellow solid (2.00 g, 83%). 1H NMR (CDCl3) δ 8.44-8.39 (m, 4H), 7.56-7.53 (m, 4H), 5.51 (s, 2H), 4.71 (s, 2H), 2.69 (s, 3H), 2.46 (s, 3H), 1.55 (s, 9H). 13C NMR (CDCl3) δ 155.6, 132.5, 131.0, 130.0, 125.8, 125.7, 125.4, 125.3, 124.9, 79.7, 47.8, 42.6, 36.9, 31.6, 28.6. IR (cm−1): 1686. HRMS (FAB) calcd for C23H28N2O2 (M+) 364.2151, found 364.2159. Anal. calcd for C23H28N2O2: C, 75.79; H, 7.74; N, 7.69. Found: C, 75.64; H, 7.71; N, 7.53.

Workup

  1. stirringstirred for 30 min
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with water (3×50 mL)
  5. dry with materialdried over MgSO4
  6. customSolvent evaporation
  7. customgave a crude product, which
  8. customwas purified on a silica gel column
  9. washeluting with MeOH/CH2Cl2 (1/2)

Sources & evidence

ORD record
ord-ba15aec70adb48eb83973ac28a8ecd42
Source dataset
uspto-grants-2005_07
Patent number
US06916660B2

Reaction notes

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