Lithium borohydride → HCID 66790672, compound

HRID 2114748Notes

Reaction equation

HRID 2114748 reaction equation
[BH4-].[Li+].C([O:5][C:6]([C@H:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[N:9]1[CH2:15][CH2:16][S:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=O)C>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][S:17][CH2:16][CH2:15][N:9]1[C:10](=[O:14])[CH2:11][CH2:12][CH2:13][C@@H:8]1[CH2:6][OH:5]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66790130HCID 66790130, compound

Product 1

HCID 66790672HCID 66790672, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Lithium borohydride (2.0 M in THF, 0.25 mL, 0.50 mmol) was added slowly to a solution of (R)-1-[2-(3-methoxycarbonyl-propylsulfanyl)-ethyl]-6-oxo-piperidine-2-carboxylic acid ethyl ester (160 mg, 0.48 mmol) in CH2Cl2 (1.5 mL) at −40° C. After 4.5 h at −40° C., the reaction was quenched by addition of a few drops of aqueous HCl (6 N) until gas evolution ceased. Solid NaHCO3 was added and the reaction mixture was filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2, gradient) afforded 33 mg (˜23%) of an inseparable mixture of desired product 4-[2-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-ethylsulfanyl]-butyric acid methyl ester and undesired product (R)-1-[2-(4-hydroxybutylsulfanyl)-ethyl]-6-oxo-piperidine-2-carboxylic acid ethyl ester.

Workup

  1. customthe reaction was quenched by addition of a few drops of aqueous HCl (6 N) until gas evolution
  2. additionSolid NaHCO3 was added
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→2% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-13dd064786d64f7d95c644c2c0bd2021
Source dataset
uspto-grants-2008_10
Patent number
US07435746B2

Reaction notes

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