Diisobutylaluminumhydride → HCID 69677723, compound

HRID 584172Notes

Reaction equation

HRID 584172 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1/[CH:14]=[CH:15]/[C:16](OCC)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1/[CH:14]=[CH:15]/[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86588503HCID 86588503, compound

Product 1

HCID 69677723HCID 69677723, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl (2E)-3-[(3R)-4-(tert-butoxycarbonyl)morpholin-3-yl]acrylate (1.0 g) in toluene (10 ml) was added diisobutylaluminum hydride (1.02 M in toluene, 7.6 ml) at −78° C.˜−40° C. After stirring for 2 hours at 0° C., the mixture was quenched with methanol (1.2 ml), and stirred for 1 hour at room temperature. After the resulting precipitate was filtered off, the filtrate was evaporated and purified by column chromatography on a silica gel using a mixture of ethyl acetate and hexane (3:7˜4:6) as eluent to give (3R)-4-(tert-butoxycarbonyl)-3-[(E)-3-hydroxy-1-propenyl]morpholine (0.71 g) as a colorless oil.

Workup

  1. customthe mixture was quenched with methanol (1.2 ml)
  2. stirringstirred for 1 hour at room temperature
  3. filtrationAfter the resulting precipitate was filtered off
  4. customthe filtrate was evaporated
  5. custompurified by column chromatography on a silica gel using
  6. additiona mixture of ethyl acetate and hexane (3:7˜4:6) as eluent

Sources & evidence

ORD record
ord-c27c1f44cd77439aacb225339381a7ec
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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