Sodium borohydride → Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate

HRID 371336Notes

Reaction equation

HRID 371336 reaction equation
[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].[BH4-].[Na+]>C(O)C>[OH:1][C:2]([CH3:27])([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][S:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20273770Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-oxoheptanoate

Product 1

HCID 20273773Methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoateYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 16 (about 4 mg) in ethanol (0.5 mL) at 0° was added sodium borohydride (3 mg). The mixture was stirred at 0° for one hour and then quenched with one drop of acetic acid. After removing ethanol, the residue was diluted with methylene chloride and washed with saturated sodium chloride. The separated aqueous layer was extracted with methylene chloride twice and the combined organic layer was dried over magnesium sulfate. Removal of the solvent gave 2.7 mg of methyl 7-[2-(2-hydroxy-2-methylheptylthio)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoate, 17. By comparison of TLC mobility, this product was determined to be identical in element content to that of Example 4.

Workup

  1. customquenched with one drop of acetic acid
  2. customAfter removing ethanol
  3. additionthe residue was diluted with methylene chloride
  4. washwashed with saturated sodium chloride
  5. extractionThe separated aqueous layer was extracted with methylene chloride twice
  6. dry with materialthe combined organic layer was dried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-d7dfa36269804f8f96af0a140e4ae333
Source dataset
uspto-grants-1985_07
Patent number
US04530933

Reaction notes

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