Hydrochloric Acid → HCID 22641504, compound

HRID 2415494Notes

Reaction equation

HRID 2415494 reaction equation
C([O:3][C:4](=O)[CH2:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:12][C:13]([CH3:17])=[N:14]2)=[CH:9][CH:8]=1)C.[BH4-].[Na+].Cl>C(O)C>[CH3:17][C:13]1[CH:12]=[C:11]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[C:10]2[C:15](=[CH:16][C:7]([O:6][CH2:5][CH2:4][OH:3])=[CH:8][CH:9]=2)[N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 69287154(2-Methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester

Product 1

HCID 22641504HCID 22641504, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a cooled (0° C.) solution of (2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-acetic acid ethyl ester (613 mg, 1.95 mmol) in ethyl alcohol (10 mL) was added sodium borohydride (506 mg, 12.84 mmol). The mixture was stirred 7 h at room temperature. Aqueous hydrochloride was added carefully (12M, 1 mL). The suspension was filtered and the solid was washed with MeOH. The solution was dried over sodium sulfate, filtered and the solvent was removed in a high vacuum to give 425 mg (80.0%) of 2-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-yloxy)-ethanol as a brown oil. ISP mass spectrum, m/e: 273.4 (M+1 calculated for C16H20N2O2: 273.4).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with MeOH
  3. dry with materialThe solution was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in a high vacuum

Sources & evidence

ORD record
ord-6a9b9ef3037547a2b5f22c69b11b627c
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

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