Imidazole → Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

HRID 1873562Notes

Reaction equation

HRID 1873562 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)C>[Si:21]([O:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 87117Methyl 4-hydroxycyclohexanecarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 22167752Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

2.00 g (11.38 mmol) of the crude product from Example 8A (90% pure) are dissolved in 50 ml of dry DMF, and 1.47 g (21.62 mmol) of imidazole and 2.40 g (15.93 mmol) of tert-butyldimethyl-silyl chloride are added. The reaction mixture is stirred at RT for 20 h. 40 ml each of diethyl ether and of saturated aqueous sodium bicarbonate solution are then added to the mixture. After phase separation, the organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The crude product is used in the next reaction without further purification.

Workup

  1. customAfter phase separation
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customThe crude product is used in the next reaction without further purification

Sources & evidence

ORD record
ord-81389788d46148849b830a9cd69f5c92
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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