Sodium Hydroxide → HCID 21932007, compound

HRID 750784Notes

Reaction equation

HRID 750784 reaction equation
[C:1]([C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([C:25]([OH:27])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:8][CH2:7][CH2:6][CH2:5]1)([OH:3])=[O:2].[OH-].[Na+].[BH4-].[Na+]>CC(O)C.O>[C:25]([C:20]1([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([OH:28])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:4]2([C:1]([OH:3])=[O:2])[CH2:8][CH2:7][CH2:6][CH2:5]2)[CH2:21][CH2:22][CH2:23][CH2:24]1)([OH:27])=[O:26]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 11545669HCID 11545669, compound

Product 1

HCID 21932007HCID 21932007, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a mixture of 1-[11-(1-carboxycyclopentyl)-6-oxoundecyl]-1-cyclopentanecarboxylic acid (5.00 g, 12.7 mmol) in iPrOH (30 mL) and H2O (30 mL) was added NaOH (1.07 g, 26.3 mmol). To the resulting clear solution, NaBH4 (0.38 g, 10.0 mmol) was added. After 19 h, the reaction mixture was concentrated in vacuo. The remaining residue was dissolved in H2O (50 mL) and acidified with aqueous HCl (6M, 15 mL). The resulting mixture was extracted with Et2O (100 mL, 2×50 mL), and the combined organic layers were washed with brine (2×50 mL), dried (Na2SO4) and concentrated in vacuo to give 1-[11-(1-carboxycyclopentyl)-6-hydroxyundecyl]-1-cyclopentanecarboxylic acid (5.18 g, 99%, contains 4% (w/w) Et2O) as a thick, light yellow oil that slowly crystallized on standing. mp=: 76-77° C. 1H NMR (CDCl3); δ=3.56 (br s, 1H), 2.16-2.11 (m, 4H), 1.64-1.61 (m, 12H), 1.51-1.18 (m, 20H). 13C NMR (CDCl3): δ=184.3 (2×), 71.4, 54.2 (2×), 39.2 (2×), 36.9 (2×), 36.2 (2×), 35.7 (2×), 29.5 (2×), 25.9 (2×), 25.2 (2×), 25.1 (2×), 25.0 (2×).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe remaining residue was dissolved in H2O (50 mL)
  3. extractionThe resulting mixture was extracted with Et2O (100 mL, 2×50 mL)
  4. washthe combined organic layers were washed with brine (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-790c3ac7490d4762ab046ff27892f868
Source dataset
uspto-grants-2008_07
Patent number
US07405226B2

Reaction notes

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