Acetic Acid → HCID 59323234, compound

HRID 2390040Notes

Reaction equation

HRID 2390040 reaction equation
[CH2:1]([CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:18])[CH:15]=2)[CH2:10][NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([N:26]([CH2:34][CH:35]=O)[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH2:19]([N:26]([CH2:34][CH2:35][N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:18])[CH:15]=2)[CH2:10]1)[C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 10868680tert-butyl benzyl(2-oxoethyl)carbamateHCID 59323144HCID 59323144, compound

Product 1

HCID 59323234HCID 59323234, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

8 mg of 3-benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline, 9.3 mg of tert-butyl benzyl(2-oxoethyl)carbamate, 11 mg of sodium triacetoxyborohydride, and 10 μL of acetic acid were dissolved in 0.5 mL of toluene, followed by continuously stirring at room temperature for 30 minutes. Water was added to the reaction liquid, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (diethyl ether:hexane=1:2) to obtain 14 mg (yield 85%) of a title compound as a yellow oily substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washthe organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customwas purified

Sources & evidence

ORD record
ord-3a29c5b63fcf4a868fe0f8c9a0ed5fa8
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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