Water → HCID 59570936, compound

HRID 2192925Notes

Reaction equation

HRID 2192925 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:16][C:15]3([CH2:28][CH2:27][CH:26]([C:29]([O-])=[O:30])[CH2:25][CH2:24]3)[O:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:7]1([C@H:13]2[C@H:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:16][C:15]3([CH2:28][CH2:27][CH:26]([CH2:29][OH:30])[CH2:25][CH2:24]3)[O:14]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86647484HCID 86647484, compound

Product 1

HCID 59570936HCID 59570936, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a mixed solution of lithium aluminum hydride (3.36 g) in THF (215 mL) was added a solution of (2S,3S)-2,3-diphenyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (43.3 g) in THF (215 mL) at an internal temperature of 10° C. or lower over 30 minutes in a methanol-ice bath, followed by stirring at an internal temperature of 10° C. or lower for 1 hour and then stirring in an ice bath for 2 hours. To the reaction mixture were sequentially added water (8.6 mL), 10% aqueous sodium hydroxide solution (8.6 mL), and water (27.5 mL) in an ice bath, followed by stirring at room temperature for 30 minutes. The solid was removed by filtration through Celite and the filtrate was concentrated to obtain [(2S,3S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-8-yl]methanol (38.4 g) as a pale peach pink oily substance.

Workup

  1. stirringstirring in an ice bath for 2 hours
  2. stirringby stirring at room temperature for 30 minutes
  3. customThe solid was removed by filtration through Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d44b09cb6b92484b9ba3443668dd86f6
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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