Water → HCID 57554657, compound

HRID 1511901Notes

Reaction equation

HRID 1511901 reaction equation
[OH:1][CH2:2][C@@:3]1([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>ClCCl>[CH:2]([C@@:3]1([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:10][CH:9]=2)[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 24741003HCID 24741003, compound

Product 1

HCID 57554657HCID 57554657, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tert-butyl (1R,3S)-1-(hydroxymethyl)-3-(4-octylphenyl)cyclopentylcarbamate (3.9 g, 9.66 mmol) was dissolved in dichloromethane (193 ml) under nitrogen to give a colorless solution. Dess-Martin periodinane (4.51 g, 10.63 mmol) (Aldrich) was added and the reaction stirred for about 3 h. LC/MS showed the reaction was complete. Methylene chloride (100 mL) and water (100 mL) were added and the layers separated and extracted with methylene chloride (2×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and evaporated to an off-white solid. The residue was purified by flash column chromatography (120 g Redi-Sep) eluting with ethyl acetate/heptane and the product fractions combined. Solvents were removed under reduced pressure to provide tert-butyl (1R,3S)-1-formyl-3-(4-octylphenyl)cyclopentylcarbamate (3.40 g, 88%) as an off white solid: LC/MS (method f) Rt=3.58 min.; MS m/z: 401.36 (M+H)+.

Workup

  1. customto give a colorless solution
  2. customthe layers separated
  3. extractionextracted with methylene chloride (2×50 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to an off-white solid
  8. customThe residue was purified by flash column chromatography (120 g Redi-Sep)
  9. washeluting with ethyl acetate/heptane
  10. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-69a106aef98a444084ca8ee22b410325
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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