Hydrochloric Acid → methyl (R,R)-2-hydroxycyclopentanecarboxylate

HRID 234795Notes

Reaction equation

HRID 234795 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10])=[O:4].Cl>CO>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[OH:10])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 11008032methyl (R,R)-2-hydroxycyclopentanecarboxylateYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methoxycarbonyl-cyclopentanone (4.26 g) was dissolved in methanol (5 mL) and 0.1 mL 1N HCl was added. The mixture was deoxygenated, 1 (36 mg) was added and the mixture was exposed to hydrogen at 40 psi and 40° in a Parr shaker apparatus. After 6 h the reaction was complete, providing a single product (4.10 g) in >95% ee: 1H NMR (CDCl3, 250 MHz) 4.40 (q, J=7.5 Hz, 1H), 3.71 (s, 3H), 2.65 (q, J=7.2 Hz, 1H), 2.1-1.5 (m, 6H).

Workup

  1. customThe mixture was deoxygenated
  2. addition1 (36 mg) was added
  3. customwas exposed to hydrogen at 40 psi and 40° in a Parr shaker apparatus

Sources & evidence

ORD record
ord-2b2a481e0f6d4b0e8ea0e0e13e9d8764
Source dataset
uspto-grants-1997_01
Patent number
US05596113

Reaction notes

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