Acetic Acid → HCID 59644966, compound

HRID 1874112Notes

Reaction equation

HRID 1874112 reaction equation
[C:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C@@H:8]([CH2:20][CH2:21][C:22](=[O:30])[C:23]([F:29])([F:28])[CH2:24][CH2:25][CH2:26][CH3:27])[C@H:7]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[C:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C@@H:8]([CH2:20][CH2:21][CH:22]([OH:30])[C:23]([F:28])([F:29])[CH2:24][CH2:25][CH2:26][CH3:27])[C@H:7]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59644965HCID 59644965, compound

Product 1

HCID 59644966HCID 59644966, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 7-[(1R,2R,3R,5S)-5-acetoxy-2-(4,4-difluoro-3-oxooctyl)-3-(2-tetrahydro pyranyloxy)cyclopentyl]heptanate (15) (71.01 g, 133.3 mmol) in methanol (284 ml) was cooled to approximately −20° C., and sodium borohydride (5.08 g, 134 mmol) was added thereto. After stirring for approximately 40 minutes, acetic acid (7.6 ml, 133 mmol) was added drop wise, and the reaction mixture was concentrated under reduced pressure. The residue was supplemented with water (325 ml) and extracted three times with ethyl acetate (228 mL). The organic layers were combined, washed with 3% aqueous sodium chloride (325 ml) and saturated aqueous sodium chloride (325 ml), and dried with anhydrous magnesium sulfate (51 g). The solution was concentrated under reduced pressure to give methyl 7-[(1R,2R,3R,5S)-5-acetoxy-2-(4,4-difluoro-3-hydroxyoctyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanate (16) (70.64 g; 132.1 mmol; yield: 99.1%) as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionextracted three times with ethyl acetate (228 mL)
  3. washwashed with 3% aqueous sodium chloride (325 ml) and saturated aqueous sodium chloride (325 ml)
  4. dry with materialdried with anhydrous magnesium sulfate (51 g)
  5. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-92af59d45ad148778444e37ba14b2eb2
Source dataset
uspto-grants-2012_11
Patent number
US08304562B2

Reaction notes

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