Sodium triacetoxyborohydride → HCID 15392197, compound

HRID 362500Notes

Reaction equation

HRID 362500 reaction equation
[CH:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]2)=[CH:5][CH:4]=1)=O.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[CH:35]=[CH:34][C:32]([NH:33][CH2:1][C:3]3[CH:12]=[C:11]4[C:6]([CH:7]=[CH:8][C:9]([C:13]#[N:14])=[CH:10]4)=[CH:5][CH:4]=3)=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 153921967-Formylnaphthalene-2-carbonitrileHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 15392197HCID 15392197, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

7-Formyl-2-naphthalenecarbonitrile obtained in Reference Example 1 (849 mg) and 1,370 mg of 4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]aniline were dissolved in 10 ml of dichloromethane and 2.7 ml of acetic acid, 1,290 mg of sodium triacetoxyborohydride was added to the solution, and the mixture was stirred at room temperature for 45 minutes. The reaction solution was washed with 2M potassium carbonate, water and 10% citric acid aqueous solution in that order, dried over sodium sulfate, and then evaporated. By recrystallizing the resulting residue from methanol, 1,698 mg of 7-[[4-[(1-t-butoxycarbonyl-4-piperidyl)oxy]anilino]methyl]-2-naphthalenecarbonitrile was obtained.

Workup

  1. washThe reaction solution was washed with 2M potassium carbonate, water and 10% citric acid aqueous solution in that order
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customBy recrystallizing the resulting residue from methanol

Sources & evidence

ORD record
ord-500be85a653d42a2bb9d13c5d69b1c59
Source dataset
uspto-grants-1999_02
Patent number
US05869501

Reaction notes

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