Methanol → HCID 66672809, compound

HRID 1869662Notes

Reaction equation

HRID 1869662 reaction equation
C([O:4][CH2:5][C@@:6]([NH:27]C(=O)C)([CH3:26])[CH2:7][CH2:8][C:9]1[N:10]([CH3:25])[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1)(=O)C.O1CCCC1.CO.O.[OH-].[Li+]>O>[NH2:27][C@:6]([CH3:26])([CH2:7][CH2:8][C:9]1[N:10]([CH3:25])[C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:13]=1)[CH2:5][OH:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66673122HCID 66673122, compound

Product 1

HCID 66672809HCID 66672809, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of (2R)-1-acetoxy-2-acetylamino-2-methyl-4-[1-methyl-5-(5-phenylpentyl)pyrrol-2-yl]butane (75.0 mg, 0.18 mmol) obtained in Example (31b) in a mixed solvent of tetrahydrofuran (1 ml) and methanol (1 ml) were added successively water (1 ml) and lithium hydroxide monohydrate (76 mg, 1.81 mmol) with stirring, and the resulting mixture was stirred at 50° C. for 6 hours. After cooling, water was adder to the reaction mixture, and the resulting mixture was extracted with dichloromethane. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a basic silica gel column (NH type) using a mixed solvent of dichloromethane and methanol (1:0-50:1) as the eluent to afford (2R)-2-amino-2-methyl-4-[1-methyl-5-(5-phenylpentyl)pyrrol-2-yl]butan-1-ol (53.6 mg, yield: 90%).

Workup

  1. stirringthe resulting mixture was stirred at 50° C. for 6 hours
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by chromatography on a basic silica gel column (NH type)

Sources & evidence

ORD record
ord-2a1445f1c2a4446d97686db6177c5882
Source dataset
uspto-grants-2009_12
Patent number
US07638551B2

Reaction notes

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