Hydrochloric Acid → HCID 21932024, compound

HRID 468024Notes

Reaction equation

HRID 468024 reaction equation
[C:1]([C:4]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]2([C:21]([OH:23])=[O:22])[CH2:20][CH2:19][CH2:18]2)[CH2:7][CH2:6][CH2:5]1)([OH:3])=[O:2].[BH4-].[Na+].Cl>[OH-].[Na+].CC(O)C>[C:21]([C:17]1([CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([OH:24])[CH2:11][CH2:10][CH2:9][CH2:8][C:4]2([C:1]([OH:3])=[O:2])[CH2:5][CH2:6][CH2:7]2)[CH2:18][CH2:19][CH2:20]1)([OH:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 11702831HCID 11702831, compound

Product 1

HCID 21932024HCID 21932024, compoundYield 103.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 1-[9-(1-carboxycyclobutyl)-5-oxononyl]-1-cyclo-butanecarboxylic acid (7.83 g, 23.1 mmol) in aqueous NaOH (1M, 70 mL) and i-PrOH (70 mL) was added NaBH4 (0.659 g, 17.3 mmol). After stirring for 3.5 h, the reaction mixture was acidified to pH˜1 with conc HCl and extracted with Et2O (1×250 mL, 2×150 mL). The combined organic layers were washed with brine (250 mL), dried (Na2SO4) and concentrated in vacuo. The remaining residue was dried under high vacuum to give 1-[9-(1-carboxycyclobutyl)-5-hydroxynonyl]-1-cyclobutanecarboxylic acid (8.17 g, 97%, contains 7% % (w/w) Et2O) as a thick, colorless oil. 1H NMR (CDCl3): δ=8.56 (br s, 3H), 3.58 (br s, 1H), 2.55-2.30 (m, 4H), 2.00-1.80 (m, 8H), 1.78 (t, J=7.7 Hz, 4H), 1.52-1.15 (m, 12H). 13C NMR (CDCl3): δ=183.0 (2×), 71.7, 47.7 (2×), 38.0 (2×), 37.1 (2×), 30.2 (2×), 30.1 (2×), 25.9 (2×), 25.0 (2×), 15.7 (2×).

Workup

  1. extractionextracted with Et2O (1×250 mL, 2×150 mL)
  2. washThe combined organic layers were washed with brine (250 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe remaining residue was dried under high vacuum

Sources & evidence

ORD record
ord-68e27afe57f3496283973eefe30fc186
Source dataset
uspto-grants-2014_01
Patent number
US08623915B2

Reaction notes

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