Sodium Hydroxide → (R)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3-yl]ethanol

HRID 1677064Notes

Reaction equation

HRID 1677064 reaction equation
C[Si](I)(C)C.C([O:13][C@@H:14]([C@H:16]1[CH2:21][O:20][CH2:19][C@@H:18]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[NH:17]1)[CH3:15])C1C=CC=CC=1.[OH-].[Na+]>ClCCl>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C@H:18]2[NH:17][C@@H:16]([C@H:14]([OH:13])[CH3:15])[CH2:21][O:20][CH2:19]2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodide4×HCID 67372082(3R,5R)-3-((R)-1-benzyloxyethyl)-5-(4-chlorophenyl)morpholine

Product 1

HCID 67371750(R)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3-yl]ethanolYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilyl iodide (3.07 mL) was added to a dichloromethane (20 mL) solution of (3R,5R)-3-((R)-1-benzyloxyethyl)-5-(4-chlorophenyl)morpholin (1.44 g). Stirring was continued for 10 hours at room temperature. Additional trimethylsilyl iodide (3.07 mL) was added, and the resultant was stirred at room temperature for 4 days. Additional trimethylsilyl iodide (3.07 mL) was further added, and stirring was continued for 1 day. Additional trimethylsilyl iodide (3.07 mL) was further added, and stirring was continued for 10 hours at room temperature. A 5 N sodium hydroxide solution was added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate. The resultant was purified with silica gel column chromatography (heptane/ethyl acetate). The title compound (903 mg) was obtained. The physical property values are as follows.

Workup

  1. stirringthe resultant was stirred at room temperature for 4 days
  2. stirringstirring
  3. waitwas continued for 1 day
  4. stirringstirring
  5. waitwas continued for 10 hours at room temperature
  6. customthe organic layer was partitioned
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customThe resultant was purified with silica gel column chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-8fe09a53f1fd454dab738b92aed705a5
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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