(1R,2S,4R)-Born-2-ylamine → (R)-bornylamine

HRID 132760Notes

Reaction equation

HRID 132760 reaction equation
[C:1]12([CH3:11])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH2:10].C12(C)C(C)(C)C(CC1)CC2N.CS(O)(=O)=O>>[C@:1]12([CH3:11])[C:7]([CH3:8])([CH3:9])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[NH2:10]

Participants

3

Reactant 2

HCID 32526(1R,2S,4R)-Born-2-ylamineHCID 17950908Bornylamine methane sulfonic acid

Product 1

HCID 211083(R)-bornylamine

Procedure

Bornylamine (X) was recycled by first adjusting the pH of the aqueous solution of bornylamine-methane sulfonic acid (XM), obtained from the previous step, to 10-13, and then extracting the free amine into MTBE. After removal of solvent, 4.308 g of (R)-bornylamine (X) was obtained (>97% pure by 1H NMR, 92.6% yield).

Workup

  1. customobtained from the previous step, to 10-13
  2. extractionextracting the free amine into MTBE
  3. customAfter removal of solvent

Sources & evidence

ORD record
ord-c0fd11cb5d4042c387c5853bf50515bc
Source dataset
uspto-grants-2008_06
Patent number
US07388098B2

Reaction notes

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