Hydrochloric Acid → 9alpha,15-Dihydroxyprostanoic acid

HRID 1580237Notes

Reaction equation

HRID 1580237 reaction equation
[OH:1][CH:2]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:3][CH2:4][C@@H:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:8](=[O:19])[CH2:7][CH2:6]1.C1C2B3C(CCC2)CCCC3CC1.[Li].[OH-].[Na+].OO.Cl>CCOCC.O1CCCC1>[OH:19][C@H:8]1[CH2:7][CH2:6][C@H:5]([CH2:4][CH2:3][CH:2]([OH:1])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 193037AY 22093HCID 70418318Lithium perhydro-9b-boraphenalylhydride

Product 1

HCID 185948159alpha,15-Dihydroxyprostanoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 433 mg. of 15-hydroxy-9-oxoprostanoic acid (Example 186) in 4.5 ml. of tetrahydrofuran, stirred in an ice-bath under nitrogen atmosphere, is added dropwise 3.7 ml. of 0.76 M lithium perhydro-9b-boraphenalylhydride. After 40 minutes at 0°C. there is added 1.62 ml. of 3N sodium hydroxide followed by 1.62 ml. of 30% hydrogen peroxide. Ether is added and the resulting solution is acidified with 2N hydrochloric acid. The ether layer is washed several times with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and taken to dryness to give 300 mg. (70%) of waxy solid; nmr 3H singlet δ 4.64 (hydroxyl and carboxyl protons), 1 H singlet 4.22 (9β-carbinolic proton, 80%), 1 H singlet 3.88 (9α-carbinolic protons, 20%), 1 H singlet 3.61 (15-carbinolic proton), and 3 H distorted triplet 0.90 (terminal methyl).

Workup

  1. additionis added dropwise 3.7 ml
  2. additionAfter 40 minutes at 0°C. there is added 1.62 ml
  3. washThe ether layer is washed several times with saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customto give 300 mg

Sources & evidence

ORD record
ord-28d9b8d5b402472a85428dc31e8f652a
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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