Hexane → Glycylbornane-10,2-sultam

HRID 842452

Reaction equation

HRID 842452 reaction equation
C[Al](C)C.CCCCCC.[C:11]123[CH2:24][S:21](=[O:23])(=[O:22])[NH:20][C@@H:12]1[CH2:13][CH:14]([C:17]2([CH3:19])[CH3:18])[CH2:15][CH2:16]3.[NH2:25][CH2:26][C:27]([O-])=[O:28].CO[2H]>C1(C)C=CC=CC=1>[NH2:25][CH2:26][C:27]([C:12]12[NH:20][S:21](=[O:23])(=[O:22])[CH2:24][C:11]31[C:17]([CH3:19])([CH3:18])[CH:14]([CH2:13]2)[CH2:15][CH2:16]3)=[O:28]

Participants

7

Reactant 5

HCID 8058HexaneHCID 26066GlycinateHCID 123113Methan(2H)olHCID 658384(-)-10,2-CamphorsultamHCID 16682925Trimethylaluminum

Product 1

HCID 70275055Glycylbornane-10,2-sultamYield 158.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
50 °C

Procedure

Over 20 minutes, 2 M trimethylaluminum in hexane (40 ml, 1.2 eq) was added to (2R)-bornane-10,2-sultam (15.7 g, 1.1 eq) in toluene (110 ml) at 0° C., then left for 30 minutes. Ethyl N-(diphenylmethylene)[1,2-13C2, 15N, 2,2-2H2]glycinate (18.1 g, 66.4 mmol) in toluene (10 ml) was added and the reaction stirred overnight. Heating to 50° C. for 3-4 hours drove the reaction to completion. Workup was effected by cooling the reaction in ice and carefully adding MeOD (20 ml). After 1 hour, D2O (30 ml) was carefully added. Filtering, extracting with ethyl acetate (2×250 ml), drying over MgSO4 and purifying by silica gel flash chromatography (Hexane: Ethyl Acetate 10:1 to 1:1) gave (2R)-N-(diphenylmethylene)[1,2-13C2, 15N, 2,2-2H2]glycylbornane-10,2-sultam (28.7 g, 99% yield) as an orange oil.

Workup

  1. waitleft for 30 minutes
  2. customthe reaction to completion
  3. temperatureby cooling
  4. customthe reaction in ice
  5. waitAfter 1 hour
  6. additionD2O (30 ml) was carefully added
  7. filtrationFiltering
  8. extractionextracting with ethyl acetate (2×250 ml)
  9. dry with materialdrying over MgSO4
  10. custompurifying by silica gel flash chromatography (Hexane: Ethyl Acetate 10:1 to 1:1)
  11. customgave (2R)-N-(diphenylmethylene)[1,2-13C2, 15N

Sources & evidence

ORD record
ord-efcf14a594d8494386a51a0b4f712840
Source dataset
uspto-grants-2002_04
Patent number
US06376253B1

Linked notes

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