Triethylamine → HCID 68810552, compound

HRID 657131Notes

Reaction equation

HRID 657131 reaction equation
[OH:1][C@H:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5][C@@H:4]([C:18]([OH:20])=[O:19])[CH2:3]1.CCN(CC)CC.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>C(Cl)(Cl)Cl>[CH3:32][C:31]([Si:28]([CH3:30])([CH3:29])[O:1][C@H:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:5][C@@H:4]([C:18]([OH:20])=[O:19])[CH2:3]1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 68994352HCID 68994352, compound

Product 1

HCID 68810552HCID 68810552, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To cis-(3RS,5RS)-5-hydroxy-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (0.78 g; 2.8 mmol) in CHCl3 was added Et3N (2.0 ml; 15 mmol), and tert-butyldimethylsilyl chloride (1.06 g; 7.0 mmol). The reaction was allowed to stir for 14 hours under N2 at room temperature. The reaction was diluted with 200 ml of CHCl3 and washed with saturated aqueous NaHCO3, 0.1 N aqueous HCl, saturated aqueous NH4Cl, and brine. The organic layer was dried with Na2SO4, and the solvents were removed to provide the desired compound (0.80 g; 73%) as a colorless oil.

Workup

  1. washwashed with saturated aqueous NaHCO3, 0.1 N aqueous HCl, saturated aqueous NH4Cl, and brine
  2. dry with materialThe organic layer was dried with Na2SO4
  3. customthe solvents were removed

Sources & evidence

ORD record
ord-9dc301bdbd9343f591b66da296c469a1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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