Citric Acid → HCID 22413608, compound

HRID 1721680Notes

Reaction equation

HRID 1721680 reaction equation
[CH:1]1([CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:14][CH:13]=2)[C:9](O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH:1]1([CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=3)=[CH:14][CH:13]=2)[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 14674838HCID 14674838, compound

Product 1

HCID 22413608HCID 22413608, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-cyclohexyl-2-(4-(2-quinolylmethoxy)phenyl)propionic acid, prepared according to the procedure of K. Mohrs et al. U.S. Pat. No. 4,970,215, (1.37 g, 3.5 mmol) in THF (40 mL) at -10° C. was added triethylamine (0.5 mL, 3.6 mmol) and then dropwise a solution of ethyl chloroformate (0.36 mL, 3.6 mmol) in THF (10 mL). The reaction was stirred for 15 minutes at -10° to -5° C. and then was allowed to warm to 0° C. To the mixture was added sodium borohydride (380 mg, 10 mmol) followed by the dropwise addition of methanol (30 mL) for 30 minutes at 0° C. The resulting mixture was stirred for an additional 20 minutes and then was neutralized with 10% citric acid and extracted with ethyl acetate (100 mL). The ethyl acetate extract was washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate to provide 1.14 g of 3-cyclohexyl-2-(4-(2-quinolylmethoxy)phenyl)propan-1-ol as an oil.

Workup

  1. stirringThe resulting mixture was stirred for an additional 20 minutes
  2. extractionextracted with ethyl acetate (100 mL)
  3. extractionThe ethyl acetate extract
  4. washwas washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 2:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-a0e0529d6d9b4af0be06edcea01d76df
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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