Water → HCID 59509754, compound

HRID 2190998Notes

Reaction equation

HRID 2190998 reaction equation
C(O)(=O)[C@@H](C1C=CC=CC=1)O.[NH2:12][CH2:13][C@:14]1([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@@H:19]2[C@H:15]1[CH:16]=[C:17]([CH2:21][CH3:22])[CH2:18]2.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[NH2:12][CH2:13][C@:14]1([CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][C@@H:19]2[C@H:15]1[CH:16]=[C:17]([CH2:21][CH3:22])[CH2:18]2

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 131730090HCID 131730090, compound

Product 1

HCID 59509754HCID 59509754, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tert-butyl [(1R,5S,6S)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate D-mandelate (4.17 g, 10 mmol) was suspended in toluene (21 ml). To the suspension, triethylamine (2.09 ml), and then water (21 ml) were added, and the mixture was stirred at room temperature. After 20 minutes, the organic layer was separated and extracted. The organic layer was washed again with water (10 ml) and then concentrated under reduced pressure to obtain the free form of tert-butyl [(1R,5S,6S)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate as an oil substance. Toluene (16 ml), and then p-toluenesulfonic acid monohydrate (2.28 g) were added thereto, and the mixture was stirred at 70° C. During the stirring, toluene (15 ml) was further added, and after 3 hours, the mixture was allowed to cool. The deposited solid was filtered, then washed with toluene, and then dried under reduced pressure to obtain [(1R,5S,6S)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetic acid p-toluenesulfonate as a white powder (3.90 g).

Workup

  1. customthe organic layer was separated
  2. extractionextracted
  3. washThe organic layer was washed again with water (10 ml)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1ebc27799714b6d93ecc5cacb02f910
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

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