Sodium borohydride → HCID 53750662, compound

HRID 1263277Notes

Reaction equation

HRID 1263277 reaction equation
[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=[CH:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][C:12](=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=[CH:4][CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54141701HCID 54141701, compound

Product 1

HCID 53750662HCID 53750662, compoundYield 139.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 14 (over 100 mg) in 3 mL of ethanol at 0° was added 45 mg of sodium borohydride. After stirring two hours at 0°, it was quenched with a few drops of acetic acid. Saturated sodium chloride was added, followed by extraction with methylene chloride three times. The combined organic layer was then dried over magnesium sulfate. Removal of the solvent gave 140 mg of 7-[2-(3-hydroxy-1-octen-1-yl)-5-oxopyrrolidin-1-yl]-6-hydroxy-1-heptanoic acid (15). IR (CH2Cl2): 3500-2600 (br), 1720, 1665 cm-1 ; PMR (CDCl3): δ6.33-5.40 (m, 5H, including --CO2H and 2--OH), 4.23-3.00 (m, 5H), 2.66-2.20 (m, 4H), 1.90-1.13 (m, 16H), and 0.93 (t, 3H); MS: m/z 338.2313 (M+ --OH), calcd. for C19H32O4N, 338.2330.

Workup

  1. customit was quenched with a few drops of acetic acid
  2. additionSaturated sodium chloride was added
  3. extractionfollowed by extraction with methylene chloride three times
  4. dry with materialThe combined organic layer was then dried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-f7674b2bbb9b4375986fb9cddcf845d4
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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