Triethylamine → 907608-98-4

HRID 409490Notes

Reaction equation

HRID 409490 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:10](O)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.ClC(OCC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([CH2:10][OH:11])[CH2:6][CH2:7][CH2:8][CH2:9]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18317887HCID 18317887, compound

Product 1

HCID 57686715907608-98-4Yield 47.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclopentane-1,1-dicarboxylic acid methyl ester (1.00 g, 5.81 mmol) and triethylamine (808 uL, 5.81 mmol) in THF (15 mL) is added isobutyl chloroformate (750 uL, 5.81 mmol) at 0° C. The mixture is stirred at 0° C. for 20 minutes. The mixture is filtrated, and the filtrate is added to a suspension of NaBH4 (242 mg) in THF (15 mL) at 0° C. The mixture is stirred at 0° C. for 3 hours and at room temperature for 12 hours. To the mixture, H2O is added and the mixture is extracted with EtOAc. The organic layer is dried over MgSO4, and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography to give 1-hydroxymethyl-cyclopentanecarboxylic acid methyl ester (433 mg, 47%); TLC (hexane/EtOAc, 1:1) Rf 0.43.

Workup

  1. filtrationThe mixture is filtrated
  2. additionthe filtrate is added to a suspension of NaBH4 (242 mg) in THF (15 mL) at 0° C
  3. stirringThe mixture is stirred at 0° C. for 3 hours and at room temperature for 12 hours
  4. additionTo the mixture, H2O is added
  5. extractionthe mixture is extracted with EtOAc
  6. dry with materialThe organic layer is dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3875dc0f7ee4cbd81a361355e44b5a3
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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