Acetic Acid → 1-Ethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine

HRID 57568Notes

Reaction equation

HRID 57568 reaction equation
[CH3:1][C:2]1([CH3:21])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[O:3]1.[CH3:22][CH:23]=O.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH2:22]([N:18]1[CH2:19][CH2:20][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([B:4]3[O:3][C:2]([CH3:21])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1)[CH3:23]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 674457864-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine

Product 1

HCID 710937421-Ethyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperidine in THF was added MeCHO (40%, 0.17 mL, 1.48 mmol) and AcOH (45 mg, 0.74 mmol), the mixture was stirred at room temperature for 20 minutes. Then the NaBH(OAc)3 (157 mg, 0.74 mmol) was added and stirred overnight. The reaction solution was poured to NaHCO3, extracted with EA, dried and concentrated to give product as white solid. MS (m/z): 316 (M+H)+.

Workup

  1. stirringstirred overnight
  2. extractionextracted with EA
  3. customdried
  4. concentrationconcentrated
  5. customto give product as white solid

Sources & evidence

ORD record
ord-06494f6e1ceb4167aeec5bc621d02a1f
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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