Triethylamine → HCID 22632413, compound

HRID 2417457Notes

Reaction equation

HRID 2417457 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27946494-{[1-(tert-Butoxycarbonyl)piperidin-4-yl]oxy}benzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 22632413HCID 22632413, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.67 g (8.3 mmol) of 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoic acid and 1.73 ml (12.5 mmol) of triethylamine were dissolved in 50 ml of THF. 0.95 ml (9.9 mmol) of ethyl chloroformate was added to the obtained solution, and they were stirred for 15 minutes. The obtained precipitate was removed by the suction filtration. 1 g of ice and 0.47 g (12.5 mmol) of sodium borohydride were added to the filtrate under cooling with ice, and they were stirred overnight. The reaction mixture was treated with ethyl acetate as the extracting solvent by an ordinary method to obtain the crude product. After the purification by the silica gel column chromatography, the title compound was obtained.

Workup

  1. customThe obtained precipitate was removed by the suction filtration
  2. temperatureunder cooling with ice, and they
  3. stirringwere stirred overnight
  4. customto obtain the crude product
  5. customAfter the purification by the silica gel column chromatography

Sources & evidence

ORD record
ord-17852133513e4799ae0bc3e443965197
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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