Lithium Hydroxide → HCID 67006858, compound

HRID 1664632Notes

Reaction equation

HRID 1664632 reaction equation
[O:1]=[C:2]1[C@H:8]2[CH2:9][C@H:4]([CH2:5][CH2:6][C@@H:7]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:3]1.[Li+].[OH-:18]>C1COCC1.O>[C:13]([O:12][C:10]([C@H:7]1[CH2:6][CH2:5][C@H:4]([OH:3])[CH2:9][C@@H:8]1[C:2]([OH:18])=[O:1])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57562755HCID 57562755, compound

Product 1

HCID 67006858HCID 67006858, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (1S,2S,5S)-7-oxo-6-oxabicyclo(3,2,1)octane-2-carboxylate was dissolved in THF—H2O. At 0° C., LiOH (3 eq.) was added and the resulting mixture was stirred at 0° C. for 2 hours. TLC showed starting material was consumed. The mixture was then acidified to pH of about 2. The product was extracted with EtOAc (×3). The combined extracts were washed with brine (×1); dried over MgSO4. After filtration, the filtrate was concentrated to give (1S,2S,5S)-2-(tert-butoxycarbonyl)-5-hydroxycyclohexanecarboxylic acid (quantitative).

Workup

  1. customwas consumed
  2. extractionThe product was extracted with EtOAc (×3)
  3. washThe combined extracts were washed with brine (×1)
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ab3d16a60dc5461889b7455b74ce2d74
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

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