(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate → Methyl (1S,3S)-3-hydroxycyclopentanecarboxylate

HRID 1643413Notes

Reaction equation

HRID 1643413 reaction equation
[C@@H:1]12[O:6][C@@H:5]1[CH2:4][CH:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]2>CC(OC)(C)C>[OH:6][C@H:1]1[CH2:5][CH2:4][C@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH2:2]1

Participants

3

Reactant 1

HCID 10374550(1R,3s,5S)-methyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 10986356Methyl (1S,3S)-3-hydroxycyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of methyl (1S,5R)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (8 g, 56.3 mmol) in MTBE (100 ml) was hydrogenated at 3 atm on Parr shaker for 12 hrs. Filtered through celite evaporated followed by chromatagraphy on a 50 g silica gel Biotage Snap cartridge with 10-50% 6:3:1 Hexane-MTBE-MeCN/Hexane to give title compound. 1H NMR (500 MHz, CDCl3) δ 1.63-1.74 (m, 3H), δ 1.78 (s, br, 1H), δ 1.82-2.07 (m, 4H), δ 2.11-2.19 (m, 1H), δ 3.09 (m, 1H), δ 3.70 (s, 3H), δ 4.48 (m, 1H)

Workup

  1. filtrationFiltered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-322b1f56ae174129abd8188c9fa41142
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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