Triacetoxyperiodinane → Benzyl 3-formylazepane-1-carboxylate

HRID 1839219Notes

Reaction equation

HRID 1839219 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]([CH2:40][OH:41])[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([O:30][C:31]([N:33]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]([CH:40]=[O:41])[CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 20598086Benzyl 3-(hydroxymethyl)azepane-1-carboxylate

Product 1

HCID 20598085Benzyl 3-formylazepane-1-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (2.78 g, 6.56 mmol) was slowly added to a stirring 0° C. solution of 3-hydroxymethyl-azepane-1-carboxylic acid benzyl ester (146) (1.2516 g, 5.02 mmol) in CH2Cl2 (18.2 mL). The reaction was stirred for 1 hour until the reaction was judged complete by HPLC. The reaction was concentrated in vacuo, and a minimal amount of CH2Cl2 was added. Et2O was added to precipitate the periodinane by-product, and the reaction was filtered, concentrated, and immediately purified through an automated silica gel column with 1:1 Hexanes:EtOAc to obtain pure 3-formyl-azepane-1-carboxylic acid benzyl ester (147) (0.3086 g) in 62% yield.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiona minimal amount of CH2Cl2 was added
  3. additionEt2O was added
  4. customto precipitate the periodinane by-product
  5. filtrationthe reaction was filtered
  6. concentrationconcentrated
  7. customimmediately purified through an automated silica gel column with 1:1 Hexanes

Sources & evidence

ORD record
ord-0f22fa5bdc7d483daae45b0b69c0499b
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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