Triethylamine → HCID 22860798, compound

HRID 1721683Notes

Reaction equation

HRID 1721683 reaction equation
[CH:1]1([C@H:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:12][CH:11]=2)[C:7](O)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.CO>[CH:1]1([C@H:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)=[CH:12][CH:11]=2)[CH2:7][OH:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 123723VeliflaponHCID 4311764Sodium borohydride

Product 1

HCID 22860798HCID 22860798, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(R)-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid (290 mg, 0.8 mmol), prepared as in step 4, and triethylamine (0.14 ml, 1.0 ml) in THF (35 ml) at -25° C. was added dropwise ethyl chloroformate (0.1 ml, 1.0 mmol). Upon completion of addition, the mixture was stirred for 15 min. and warmed to 0° C. Sodium borohydride (150 mg, 4.0 mmol) was added followed by very slow addition of methanol (15 ml). The reaction was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (silica gel, hexane-ethyl acetate 2:1) to afford 180 mg of 2-(R)-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)ethan-1-ol.

Workup

  1. additionUpon completion of addition
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, hexane-ethyl acetate 2:1)

Sources & evidence

ORD record
ord-6145e29bf1da4b39af5356f7b88df027
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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