1H,2H,2AH,3H,4H,8BH-Naphtho[1,2-B]azet-2-one → methyl rac-(1S,2S)-1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylate hydrochloride

HRID 64419Notes

Reaction equation

HRID 64419 reaction equation
[NH:1]1[C:4](=[O:5])[CH:3]2[CH2:6][CH2:7][C:8]3[C:13]([CH:2]12)=[CH:12][CH:11]=[CH:10][CH:9]=3.[ClH:14].[CH3:15][OH:16]>>[ClH:14].[NH2:1][CH:2]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:3]1[C:4]([O:16][CH3:15])=[O:5]

Participants

3

Reactant 2

HCID 3002861H,2H,2AH,3H,4H,8BH-Naphtho[1,2-B]azet-2-oneHCID 21893726Hydrochloride methanol

Product 1

HCID 86713429methyl rac-(1S,2S)-1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylate hydrochloride

Conditions

Temperature
90 °C

Procedure

To 2.36 g of 2a,3,4,8b-tetrahydronaphtho[1,2-b]azet-2(1H)-one was added 50 ml of a 10% hydrogen chloride/methanol solution, followed by stirring at 90° C. for 6 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure. To the obtained residue were added methanol and diethyl ether, and the insoluble material was collected by filtration and dried to obtain 3.08 g of methyl rac-(1S,2S)-1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylate hydrochloride.

Workup

  1. customAfter leaving
  2. temperatureto be cooled
  3. customthe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue were added methanol and diethyl ether
  5. filtrationthe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-8f1e3bd1cf164e369dba1efa3822e546
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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