Methanol → HCID 89438130, compound

HRID 444806Notes

Reaction equation

HRID 444806 reaction equation
C([O:8][CH2:9][C@@:10]12[CH2:19][C:18]([F:21])([F:20])[CH2:17][C@@H:11]1[C:12]([CH2:15][OH:16])=[N:13][O:14]2)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO>ClCCl>[F:21][C:18]1([F:20])[CH2:17][C@@H:11]2[C:12]([CH2:15][OH:16])=[N:13][O:14][C@:10]2([CH2:9][OH:8])[CH2:19]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 89438328HCID 89438328, compound

Product 1

HCID 89438130HCID 89438130, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

To a solution of rac-((3aR,6aR)-6a-(benzyloxymethyl)-5,5-difluoro-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazol-3-yl)methanol (1.52 g, 5.11 mmol) in dichloromethane (23 ml) was added dropwise at −70° C. boron trichloride (1 M in dichloromethane) (15.3 ml, 15.3 mmol). The reaction mixture was stirred at −70° C. for 1 hour, then allowed to warm to 0° C. within another hour. The reaction mixture was quenched with methanol (10 ml) at −70° C., stirred for 30 minutes at room temperature and evaporated to dryness. The residue was purified by chromatography with a 9:1-mixture of dichloromethane and methanol to give rac-((3aR,6aR)-5,5-difluoro-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole-3,6a-diyl)dimethanol (880 mg, 83% yield) as a light brown solid. MS: m/z=208.1 [M+H]+.

Workup

  1. temperatureto warm to 0° C. within another hour
  2. customThe reaction mixture was quenched with methanol (10 ml) at −70° C.
  3. stirringstirred for 30 minutes at room temperature
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography with a 9

Sources & evidence

ORD record
ord-b4ffd6951382450a87d0345e5cb88ca9
Source dataset
uspto-grants-2013_07
Patent number
US08476264B2

Reaction notes

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