Acetic Acid → [4-(2-Methoxy-5-pyridin-4-yl-benzylamino)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 2389718Notes

Reaction equation

HRID 2389718 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:22][C:19]=1[CH:20]=O.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH2:20][C:19]2[CH:22]=[C:23]([C:26]3[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=3)[CH:24]=[CH:25][C:18]=2[O:17][CH3:16])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 105605352-Methoxy-5-(pyridin-4-yl)benzaldehydeHCID 178418966HCID 178418966, compound

Product 1

HCID 59683557[4-(2-Methoxy-5-pyridin-4-yl-benzylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A stirred suspension of amine (295) (131 mg, 0.61 mmol) and aldehyde (296) (130 mg, 0.61 mmol) in THF (1 mL) and toluene (1 mL) was treated with AcOH (42 μL, 0.73 mmol) at RT. After stirring 1.5 h, the resultant suspension was treated with sodium triacetoxyborohydride (181 mg, 0.86 mmol) and stirred for 18 h. The reaction was diluted with aqueous NaHCO3 and extracted into EtOAc. The organic phase was dried (Na2SO4), filtered, the solvent removed in vacuo and the residue chromatographed with 10% MeOH in EtOAc to afford the title compound.

Workup

  1. stirringstirred for 18 h
  2. extractionextracted into EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customthe residue chromatographed with 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-38efdb884e0b45e9b42a8019c306a29a
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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