Sodium periodate → 3-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506373Notes

Reaction equation

HRID 1506373 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]([OH:32])CO)=[CH:23][CH:22]=5)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:14][CH2:15][C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[O:32])=[CH:23][CH:22]=5)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 671718521-(3-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol

Product 1

HCID 866698873-(2-(1-(4-Fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(3-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethane-1,2-diol (Preparation 26B, 0.097 g, 0.223 mmol) in methanol (2 mL) at 0° C. was added a solution of sodium periodate (0.057 g, 0.268 mmol) in water (2 mL) dropwise. The white heterogeneous reaction mixture was stirred for 40 mins. at 0° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with brine, dried over sodium sulfate, concentrated, dried in vacuo to yield 3-(2-(1-(4-fluorophenyl)cyclohexyl)ethyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde. LC/MS M+1=402.23.

Workup

  1. customThe white heterogeneous reaction mixture
  2. customat 0° C. and partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1a5129683bbe485fafc31387cfad825d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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