Sodium Bicarbonate → Methyl 1-{[4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidin-1-yl]methyl}-cyclobutanecarboxylate

HRID 2410325Notes

Reaction equation

HRID 2410325 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[C:13]3[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][N:10]=2)[CH2:3][CH2:2]1.[CH:24]([C:26]1([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27]1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[F:23][C:20]([F:21])([F:22])[CH2:19][O:18][C:14]1[C:13]2[C:9]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][N:1]([CH2:24][C:26]4([C:30]([O:32][CH3:33])=[O:31])[CH2:29][CH2:28][CH2:27]4)[CH2:2][CH2:3]3)=[N:10][O:11][C:12]=2[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15656335Methyl 1-formylcyclobutane-1-carboxylateHCID 693177283-(Piperidin-4-ylmethoxy)-4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazole

Product 1

HCID 69316237Methyl 1-{[4-({[4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazol-3-yl]oxy}methyl)piperidin-1-yl]methyl}-cyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3-(piperidin-4-ylmethoxy)-4-(2,2,2-trifluoroethoxy)-1,2-benzisoxazole (0.33 g, 1.0 mmol, EXAMPLE 2, Step 2) and methyl 1-formylcyclobutanecarboxylate (0.17 g, 1.2 mmol, J. Org. Chem. 1993, 58, 6843-6850) in dichloromethane (5 mL) was added sodium triacetoxyborohydride (0.42 g, 2.0 mmol) at room temperature. After being stirred at room temperature for 16 h, sat. aq. sodium hydrogencarbonate (20 mL) was added to the mixture. The mixture was extracted with dichloromethane (30 mL×2). The combined extract was dried over magnesium sulfate and concentrated in vacuo to give 0.46 g (quant.) of the title compound as a colorless oil.

Workup

  1. extractionThe mixture was extracted with dichloromethane (30 mL×2)
  2. extractionThe combined extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a57f0cefc7c4291a53574b4c1dc5767
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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