HCID 86761718, compound → HCID 59509754, compound

HRID 2190996Notes

Reaction equation

HRID 2190996 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[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(OCC)(=O)C>[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

3

Reactant 1

HCID 86761718HCID 86761718, compound

Product 1

HCID 59509754HCID 59509754, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl [(1R*,5S*,6S*)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate p-toluenesulfonate was suspended in ethyl acetate (20 v/w). The suspension was separated into aqueous and organic layers by the addition of an aqueous sodium bicarbonate solution (4 v/w) to obtain the free form of tert-butyl [(1R*,5S*,6S*)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate. To this tert-butyl [(1R*,5S*,6S*)-6-aminomethyl-3-ethylbicyclo[3.2.0]hept-3-en-6-yl]acetate (200 mg, 0.754 mmol), diisopropyl ether (IPE) or acetonitrile (MeCN) (1.0 mL, 5.0 v/w), and then optically active carboxylic acid (0.5 eq.) were added, and the mixture was stirred at room temperature. The deposited crystal was filtered and washed with the solvent (0.5 mL, 2.5 v/w) used. The obtained crystal was dried under reduced pressure to obtain the corresponding salt form at the yield and optical purity shown in Table 1 below.

Workup

  1. customThe suspension was separated into aqueous and organic layers
  2. additionby the addition of an aqueous sodium bicarbonate solution (4 v/w)

Sources & evidence

ORD record
ord-b4bce6f242dc49cebb069f2ab332f9c8
Source dataset
uspto-grants-2012_12
Patent number
US08324425B2

Reaction notes

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