Water → Boc-1(S)-Cyclohexylmethyl-2(R,S)-hydroxy-4-(2-pyridyl)butylamine

HRID 1722269Notes

Reaction equation

HRID 1722269 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[C:8]([NH:15][C@H:16]([CH:24]1[CH2:26][O:25]1)[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O>C1COCC1>[C:8]([NH:15][C@@H:16]([CH2:17][CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH:24]([OH:25])[CH2:26][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 79752-MethylpyridineHCID 13892786Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine

Product 1

HCID 131716032Boc-1(S)-Cyclohexylmethyl-2(R,S)-hydroxy-4-(2-pyridyl)butylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

220 μl of 2-picoline (2 eq) are deprotonated in analogy to Example (6c). Then 300 mg of Boc-2-cyclohexyl-1(S)-oxiran-2(R,S)-ylethylamine in THF are added dropwise at -60° C. After 1 h, H2O is added, and the mixture is extracted 3 times with EA. The organic phases are dried with Na2 so4 and then concentrated, and the title compound is isolated by chromatography on SiO2 with EA/H 2:1 as eluent.

Workup

  1. extractionthe mixture is extracted 3 times with EA
  2. customThe organic phases are dried with Na2 so4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0543f17795374bdb91ec108d7f074f8b
Source dataset
uspto-grants-1989_08
Patent number
US04855286

Reaction notes

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