Hydrochloric Acid → HCID 16662660, compound

HRID 548639Notes

Reaction equation

HRID 548639 reaction equation
[BH4-].[Li+].[CH3:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:23](=[O:24])[CH2:22][CH:21]([C:25](OC)=[O:26])[CH2:20]2)=[CH:15][CH:14]=1.Cl.[OH-].[Na+]>O1CCCC1.CO>[OH:26][CH2:25][CH:21]1[CH2:20][N:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][N:5]3[CH2:6][CH2:7][CH2:8][CH:4]3[CH3:3])=[CH:18][CH:17]=2)[C:23](=[O:24])[CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 57550261HCID 57550261, compound

Product 1

HCID 16662660HCID 16662660, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Lithium borohydride (0.1 g, 4.92 mmol, 1.8 eq) is added to a solution of methyl 1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-5-oxopyrrolidine-3-carboxylate a54 (0.99 g, 2.73 mmol, 1 eq) in tetrahydrofuran (20 ml) and methanol (0.35 ml). The mixture is stirred at 75° C. for 1 h, then cooled to 0° C. and a solution of 1 M hydrochloric acid is added. A solution of 2M sodium hydroxide is then added to reach a pH of 10. The aqueous layer is extracted twice with ethyl acetate, then the organic layers are dried over magnesium sulfate, and concentrated under vacuum to give 0.79 g of 4-(hydroxymethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 72 as a colorless oil.

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe aqueous layer is extracted twice with ethyl acetate
  3. dry with materialthe organic layers are dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8c45f7c701654165801f42b4caa5b549
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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