Sodium borohydride → HCID 54468844, compound

HRID 1263279Notes

Reaction equation

HRID 1263279 reaction equation
[OH:1][C:2]([CH3:28])([C:21]([F:27])([F:26])[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][C:2]([CH3:28])([C:21]([F:27])([F:26])[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 54319933HCID 54319933, compound

Product 1

HCID 54468844HCID 54468844, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 20 (24 mg, 0.059 mmol) in ethanol (2 mL) at 0° was added sodium borohydride (9 mg, 0.238 mmol). The reaction mixture was stirred at 0° for one hour before it was quenched with two drops of acetic acid. It was then diluted with saturated sodium chloride solution and extracted with chloroform three times. The combined organic layer was dried over magnesium sulfate. Purification of the crude product on TLC plates afforded 8 mg of 7-[2-(3-hydroxy-3-methyl-4,4-difluoro-1-octen-1-yl)-5-oxopyrrolidin-1-yl]-6-hydroxyheptanoic acid (21). IR (CH2Cl2): 3500-3200 (br), 1720, 1660 cm-1 ; PMR (CDCl3): δ5.95-5.60 (m, 2H), 4.40-2.80 (m, 4H), 2.60-1.20 (m, 21H), and 0.97 (t, 3H).

Workup

  1. customwas quenched with two drops of acetic acid
  2. additionIt was then diluted with saturated sodium chloride solution
  3. extractionextracted with chloroform three times
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. customPurification of the crude product on TLC plates

Sources & evidence

ORD record
ord-e980805963e54e49b72c7ecafd883de0
Source dataset
uspto-grants-1984_06
Patent number
US04456613

Reaction notes

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