Acetic Acid → HCID 86757713, compound

HRID 1250207Notes

Reaction equation

HRID 1250207 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@:15]23[CH2:24][C:23]4[N:25]=[C:26]5[C:31](=[CH:32][C:22]=4[CH2:21][C@H:20]2[CH2:19][NH:18][CH2:17][CH2:16]3)[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:33]1([CH:36]=O)[CH2:35][CH2:34]1.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH:33]1([CH2:36][N:18]2[CH2:17][CH2:16][C@:15]3([C:11]4[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH:10]=4)[C@@H:20]([CH2:21][C:22]4[CH:32]=[C:31]5[C:26]([CH:27]=[CH:28][CH:29]=[CH:30]5)=[N:25][C:23]=4[CH2:24]3)[CH2:19]2)[CH2:35][CH2:34]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 516892Sodium BicarbonateHCID 86757711HCID 86757711, compound

Product 1

HCID 86757713HCID 86757713, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(4aR, 12aR)-4a-(3-benzyloxyphenyl)-1,2,3,4,4a,5,12,12a-octahydroquinolino[2, 3-g]isoquinoline (84 mg), and cyclopropanecarboaldehyde (0.0305 ml, 0.40 mmol) were dissolved in dry THF (4 ml), and triacetoxysodium borohydride (84. 8 mg, 0.40 mmol) and acetic acid (0.0126 ml, 0.22 mmol) were added to the resultant solution, followed by stirring at room temperature for 2 hours. A saturated aqueous sodium bicarbonate solution (30 ml) and water (30 ml) were then added to the solution, and the resultant mixture was extracted with chloroform (100 ml, twice). The organic layers were dried over sodium sulfate, and then concentrated. The residue was purified by using a silica gel column to obtain (4aR, 12aR)-2-cyclopropylmethyl-4a-(3-benzyloxyphenyl)-1,2,3,4,4a,5,12,12a-octahydroquinolino[2, 3-g]isoquinoline (78 mg, 82% in two steps).

Workup

  1. extractionthe resultant mixture was extracted with chloroform (100 ml
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-0f9a415ae4a24cf29d0861592808daf6
Source dataset
uspto-grants-2002_01
Patent number
US06337330B1

Reaction notes

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