Acetic Acid → HCID 21064717, compound

HRID 1243784Notes

Reaction equation

HRID 1243784 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=1)[OH:6].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.CO>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH:3][CH2:4][CH:5]([OH:6])[C:7]2[CH:12]=[CH:11][N:10]=[C:9]([S:13][CH3:14])[N:8]=2)[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 21928144HCID 21928144, compound

Product 1

HCID 21064717HCID 21064717, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-1-(2-methylsulfanyl-pyrimidin-4-yl)-ethanol dihydrochloride salt (0.339 g, 1.83 mmol) was dissolved into a minimum of MeOH and diluted with 10 mL of THF. To this was added t-butyl-4-oxo-1-piperidinecarboxylate (0.478 g, 2.40 mmol), AcOH (0.458 mL, 8.00 mmol) and sodium triacetoxyborohydride (1.696 g, 8.00 mmol) and the reaction was stirred overnight. LC-MS analysis indicated complete consumption of the starting material. The mixture was concentrated on a rotary evaporator, the residue dissolved in CH2Cl2 and applied to a SiO2 column and purified (0–10% MeOH/CH2Cl2) to give 511.0 mg, 57.8% yield of 4-[2-hydroxy-2-(2-methylsulfanyl-pyrimidin-4-yl)-ethylamino]-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customconsumption of the starting material
  2. concentrationThe mixture was concentrated on a rotary evaporator
  3. dissolutionthe residue dissolved in CH2Cl2
  4. custompurified (0–10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fad307d41b3b48ba803c64cbd65b1427
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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