Nitrogen → Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

HRID 1169018Notes

Reaction equation

HRID 1169018 reaction equation
[C@:1]12([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].N#N>C1(C)C=CC=CC=1.C1COCC1>[CH3:9][C:8]1([CH3:10])[C:1]2([CH2:11][S:12]([OH:15])(=[O:14])=[O:13])[C:2]([CH2:4][CH:5]1[CH2:6][CH2:7]2)=[O:3]

Participants

5

Reactant 2

HCID 947NitrogenHCID 218580(1S)-(+)-Camphor-10-sulphonic acid2×

Product 1

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-Yield 99%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Thirty (30) g of the compound of Formula II and 0.386 g (2 mole %) of (1S)-(+)-10-camphorsulfonic acid (CSA) was charged in a 500 mL 3 necked round bottom flask equipped with a thermometer, N2 inlet and addition funnel. 111 mL of dry THF was charged to dissolve the 30 g of the compound Formula II, and the (1S)-(+)-10-camphorsulfonic acid at about 20 to 25° C. 2.2 mL of pre formed (R)-MCBS catalyst in toluene (3 mole %) was charged. 39.9 mL of 1M borane THF complex in THF solution was slowly charged over 1.5 hours at a temperature range between about 23 and 28° C. The batch was sampled for HPLC to monitor the progress of the reaction. After the reaction was judged complete, using the same subsequent procedure as described in Example 1 (i.e. quenching with MeOH, vacuum concentration of the batch, etc., but in appropriate ratios of reagents for this example), the compound of Formula I was obtained. Results varied, but in general, ˜99% yield and ˜94% de were obtained.

Workup

  1. customat about 20 to 25° C
  2. additionwas charged
  3. aliquotThe batch was sampled for HPLC
  4. customthe progress of the reaction
  5. customquenching with MeOH, vacuum concentration of the batch, etc.
  6. customResults
  7. customin general, ˜99% yield and ˜94% de were obtained

Sources & evidence

ORD record
ord-45007ba3e7134a1d8b4faa96b07c0694
Source dataset
uspto-grants-2003_09
Patent number
US06627757B2

Reaction notes

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