Benzyl Alcohol → (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarbonyl azide

HRID 2179733Notes

Reaction equation

HRID 2179733 reaction equation
[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8](O)=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2].CCN(CC)CC.ClC(OCC)=O.[N-:26]=[N+:27]=[N-:28].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].C(O)C1C=CC=CC=1>CC(C)=O.O>[C:1]([C@@H:4]1[CH2:7][C@H:6]([C:8]([N:26]=[N+:27]=[N-:28])=[O:9])[C:5]1([CH3:12])[CH3:11])(=[O:3])[CH3:2]

Participants

9

Reactant 6

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24436Sodium SulfateHCID 33557Sodium AzideHCID 10630987(1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid

Product 1

HCID 58110969(1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarbonyl azideYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred solution of (1S,3R)-3-acetyl-2,2-dimethylcyclobutanecarboxylic acid (1.0 g, 5.88 mmol) in acetone (20 ml), Et3N (1.6 ml, 11.76 mmol) and ethyl chloroformate (1.12 ml, 11.76 mmol) were added slowly by portion wise at about 0° C. and stirred for about 3 hours. After completion of the reaction (monitored by TLC), NaN3 (0.84 g, 12.93 mmol) dissolved in minimum amount of water was added to reaction mixture at 0° C. and the reaction mixture was allowed to stir at room temperature for about 1.5 hours. After completion of the reaction (monitored by TLC), the reaction mixture was extracted with DCM and washed with water, brine and dried over Na2SO4 and benzyl alcohol (0.95 ml, 8.82 mmol) then the solvent was evaporated and the crude product was processed for next reaction immediately without characterization (considering as 100% yield proceeded for next reaction). Crude wt: 1.147 g (100% yield).

Workup

  1. additionwas added to reaction mixture at 0° C.
  2. stirringto stir at room temperature for about 1.5 hours
  3. customAfter completion of the reaction (monitored by TLC)
  4. extractionthe reaction mixture was extracted with DCM
  5. washwashed with water, brine
  6. customthe solvent was evaporated
  7. customthe crude product was processed for next reaction immediately without characterization (considering as 100% yield proceeded for next reaction)

Sources & evidence

ORD record
ord-efebcce0c8f8490da331a737ee2f0d72
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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