Water → HCID 22882486, compound

HRID 863213Notes

Reaction equation

HRID 863213 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:20])([CH3:19])[C:15](OC)=[O:16])[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:20])([CH3:19])[CH2:15][OH:16])[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22882590HCID 22882590, compound

Product 1

HCID 22882486HCID 22882486, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 85.5 g of methyl 3-[3-tert-butoxycarbonyl-2,2-dimethyl-1,3-oxazolidine-4(S)-yl]-2,2-dimethyl-propionate in 300 ml of tetrahydrofuran is added to a suspension of 22 g of lithium aluminium hydride in 700 ml of tetrahydrofuran at -10° C. and the mixture is then stirred at 0° C. for 30 min. Thereafter, 22 ml of water, 22 ml of a 5N sodium hydroxide solution and 66 ml of water are added dropwise in succession at 0° C. and the mixture is subsequently stirred for 30 min. The suspension is filtered over Hyflo® and evaporated. After drying with sodium sulfate in methylene chloride, the title compound is obtained in the pure form: white crystals; mp. 45°-6° C.; Rf (A)=0.53, Rf (D)=0.18; [α]D =+52.8 (c=0.91 in CHCl3); FAB-MS: (M+H)+ =288; anal. calc. for C15H29NO4 : C 62.69%, H 10.17%, N 4.87%; found C 62.88%, H 10.11%, N 4.86%.

Workup

  1. stirringthe mixture is subsequently stirred for 30 min
  2. filtrationThe suspension is filtered over Hyflo®
  3. customevaporated
  4. dry with materialAfter drying with sodium sulfate in methylene chloride

Sources & evidence

ORD record
ord-a92b16e396d84d23ad04527d6f843ada
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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