Methanol → (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoic acid

HRID 2269350Notes

Reaction equation

[OH:1][C@H:2]([CH3:21])[C@@H:3]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[C:4]([O:6]C)=[O:5].O.[OH-].[Li+].CO>C1COCC1.O>[OH:1][C@H:2]([CH3:21])[C@@H:3]([CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:14]1)[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoate (4.17 g, 0.014 mol) and lithium hydroxide monohydrate (0.59 g, 0.014 mol) is stirred at 25° C. in a mixture of THF (30 mL), methanol (15 mL) and water (15 mL) for 72 h. The reaction is not complete and an additional 0.88 g (0.021 mol) of lithium hydroxide monohydrate in water (10 mL) is added. After 6 h an additional 0.59 g (0.014 mol) of solid lithium hydroxide monohydrate and the mixture is stirred at 25° C. for 18 h. The mixture is concentrated in vacuo and the residue is taken up in water, chilled in an ice-bath and the pH is adjusted to 2 with sodium bisulfate. The mixture is extracted with dichloromethane. The combined extracts were washed with saturated sodium chloride, dried over sodium sulfate and concentrated in vacuo to give 3.43 g (89%) of (2R,3R)-3-hydroxy-2-(4-phenylcyclohexylmethyl)butanoic acid as a yellow solid.

Workup

concentrationThe mixture is concentrated in vacuo
temperaturechilled in an ice-bath
extractionThe mixture is extracted with dichloromethane
washThe combined extracts were washed with saturated sodium chloride
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a3968a2575be41d6a32bf969b4a23bf1
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329400B1

Reaction notes

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