Tert-Butylamine → 2-Cyclohexylsuccinic acid monomethyl ester

HRID 1533498Notes

Reaction equation

HRID 1533498 reaction equation
C(N)(C)(C)C.[CH3:6][O:7][C:8](=[O:20])[C:9](=[C:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12].[H][H]>CO>[CH3:6][O:7][C:8](=[O:20])[CH:9]([CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[CH2:10][C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 127350342-Cyclohexylidenesuccinic acid 1-methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 98157692-Cyclohexylsuccinic acid monomethyl esterYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The tert-butylamine salt of 2-cyclohexylidenesuccinic acid 1-methyl ester (0.91 g, 3.2 mmol) was placed in a 60 mL high pressure hydrogenation vessel and the vessel was purged with hydrogen (by pressurizing and venting three times with 10 bar of hydrogen). Methanol (9 mL, previously degassed by bubbling nitrogen for one hour at room temperature under stirring) was added through the solvent port and the vessel was then cooled to 0° C. A solution of [Rh(COD)(RR)Me-BPE]OTf (0.004 g, 0.0065 mmol, substrate/catalyst: 500/1) in methanol (1 mL) was added and the reactor was charged with 10 bar of hydrogen. The reaction was stirred at 0° C. for 20 hours, then the solvent was evaporated under reduced pressure and the residue was partitioned between HCl 2N (20 mL) and ethyl acetate (20 mL). The organic layer was separated, dried over MgSO4, evaporated to give 0.75 g of 2-cyclohexylsuccinic acid monomethyl ester as a pale yellow oil (yield 82%). The enantiomeric excess of 2-(R)-cyclohexylsuccinic acid 1-methyl ester was 96% by GC.

Workup

  1. customthe vessel was purged with hydrogen (by pressurizing and venting three times with 10 bar of hydrogen)
  2. customMethanol (9 mL, previously degassed
  3. customby bubbling nitrogen for one hour at room temperature
  4. additionwas added through the solvent port
  5. stirringThe reaction was stirred at 0° C. for 20 hours
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was partitioned between HCl 2N (20 mL) and ethyl acetate (20 mL)
  8. customThe organic layer was separated
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-27660ac4ad514f05a9aff16b84d3b565
Source dataset
uspto-grants-2001_03
Patent number
US06207853B1

Reaction notes

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