Water → HCID 57263166, compound

HRID 2388669Notes

Reaction equation

HRID 2388669 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][C@H:9]1[C:18](O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[OH:19][CH2:18][C@@H:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 40425216(2S)-1-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Product 1

HCID 57263166HCID 57263166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (5 g, 18.03 mmol) was dissolved in tetrahydrofuran (40 ml) and the mixture was cooled. Boron hydride-tetrahydrofuran complex (27 ml, 1 mol/l in tetrahydrofuran) was cautiously added dropwise at 0° C. and the mixture was then stirred at room temperature for 15 h. The reaction mixture was cooled again and water (8 ml) was slowly added dropwise at 0° C. Potassium carbonate (4.21 g, 30.65 mmol) was then added and the mixture was stirred for 30 min. After phase separation the aqueous phase was extracted with diethyl ether (2×30 ml) and the combined organic phases were washed with saturated sodium chloride solution (30 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1.

Workup

  1. temperaturethe mixture was cooled
  2. temperatureThe reaction mixture was cooled again
  3. stirringthe mixture was stirred for 30 min
  4. customAfter phase separation the aqueous phase
  5. extractionwas extracted with diethyl ether (2×30 ml)
  6. washthe combined organic phases were washed with saturated sodium chloride solution (30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 2/1

Sources & evidence

ORD record
ord-fb32430a42a44788a7c1fde72d6dc6e9
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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