Hydrochloric Acid → 1-Aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl-naphthalene hydrochloride

HRID 54128Notes

Reaction equation

HRID 54128 reaction equation
C(OC([NH:8][CH2:9][C:10]1[C:19]2[C:14](=[C:15]([O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:16]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[CH2:13][CH:12]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:11]=1)=O)(C)(C)C.[ClH:40]>O1CCOCC1>[ClH:40].[NH2:8][CH2:9][C:10]1[C:19]2[C:14](=[C:15]([O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[C:16]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[CH2:13][CH:12]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19961074N-t-Butyloxycarbonyl-1-aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl naphthalene

Product 1

HCID 199612231-Aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl-naphthalene hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-t-Butyloxycarbonyl-1-aminomethyl-5,6-bis(trimethylacetoxy)-3-phenyl-3,4-dihydronaphthalene (14 g, 26 mmol), from Step 2, was dissolved in 75 mL of dioxane and saturated with anhydrous hydrogen chloride. The reaction mixture was stirred for 2 h and concentrated in vacuo. The solid residue was dissolved in a minimum amount of methanol and the methanol solution was added dropwise to an excess amount (500 mL) of diethyl ether. The precipitate was filtered, washed with diethyl ether and dried to give 9.1 g (90% yield) of 1-aminomethyl-5,6-bis(trimethylacetoxy)-3-phenyl-3,4-dihydronaphthalene hydrochloride as a white powder, m.p. 210°-212° C.; 1H NMR (d6 -DMSO) δ: 1.25 (s, 9H), 1.28 (s, 9H), 2.61 (dd, 1H), 2.89 (dd, 1H), 3.75-3.85 (m, 1H), 3.99 (s, 2H), 6.28 (d, 2H), 7.15 (d, 1H), 7.2-7.35 (m, 5H), 7.37 (d, 1H), 8.37 (br s, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe solid residue was dissolved in a minimum amount of methanol
  3. additionthe methanol solution was added dropwise to an excess amount (500 mL) of diethyl ether
  4. filtrationThe precipitate was filtered
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-2192c68811c64f79b4f3a5e44c55e488
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Reaction notes

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