Sodium borohydride → 7-[2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl ester

HRID 2052900Notes

Reaction equation

HRID 2052900 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH:17]([CH2:18][CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][CH2:14][C:13]1=[O:27]>CO.C(Cl)Cl>[CH3:3][O:4][C:5](=[O:28])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 100218997-[2-Oxo-6-(3-oxooctyl)-piperidin-1-yl]-heptanoic acid methyl ester

Product 1

HCID 100446137-[2-(3-Hydroxy-octyl)-6-oxo-piperidin-1-yl]-heptanoic acid methyl esterYield 61%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (24 mg, 0.63 mmol), followed by MeOH (2 drops), was added to a solution of 7-[2-oxo-6-(3-oxo-octyl)-piperidin-1-yl]-heptanoic acid methyl ester (23 mg, 0.063 mmol) in CH2Cl2 (1.0 mL) at 0° C. The mixture was allowed to warm to rt. After 4 h at rt, the reaction was quenched with HCl (11.0M aqueous) and extracted with EtOAc (3×10 mL). The combined organic phase was washed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL) then dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 14 mg (61%) of the title compound.

Workup

  1. customthe reaction was quenched with HCl (11.0M aqueous)
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic phase was washed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL)
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-67fe7773134c41debb65002de76f75bb
Source dataset
uspto-grants-2008_02
Patent number
US07326716B2

Reaction notes

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