2-(Methylamino)ethanol → HCID 71238254, compound

HRID 55883Notes

Reaction equation

HRID 55883 reaction equation
[CH2:1]([N:8]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9]1[CH:10]=[CH:11][C:12]([CH:15]=O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][NH:25][CH2:26][CH2:27][OH:28].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O.C(O)(=O)C>[CH2:1]([N:8]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:9]1[CH:10]=[CH:11][C:12]([CH2:15][N:25]([CH3:24])[CH2:26][CH2:27][OH:28])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86676172HCID 86676172, compound

Product 1

HCID 71238254HCID 71238254, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 39 (600 mg, 2.0 mmol) in THF (25 mL) was added 2-(methyl amino) ethanol (224 mg, 3.0 mmol) and a catalytic amount of acetic acid (0.1 mL) and cooled to 0° C. Na(OAc)3BH (1 g, 5.0 mmol) was added portion wise and the reaction mixture allowed to warm and stired at rt for 3 h. The reaction mixture was neutralized by using NaHCO3 (aq), diluted with water (25 mL, 1:3 dilution), extracted with EtOAc (2×100 mL), the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated. The crude compound was purified by column chromatography (neutral alumina, eluted with 5% MeOH/CHCl3) to obtain compound 40 (400 mg, 55%) as a brown solid. Rf: 0.3 (10% MeOH/CHCl3); (m/z): 362 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 7.91 (1H, d, J=2.8 Hz), 7.35-7.22 (10H, m), 7.12 (1H, d, J=8.8 Hz), 7.02 (1H, dd, J=2.8, 8.8 Hz), 4.72 (4H, s), 4.37 (1H, br s), 3.46-3.44 (4H, m), 2.40 (2H, t, J=6.4 Hz), 2.13 (3H, S).

Workup

  1. temperatureto warm
  2. extractionextracted with EtOAc (2×100 mL)
  3. washthe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude compound was purified by column chromatography (neutral alumina, eluted with 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-f62cfe794fd3481889de7bbba6e5b838
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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