Hydrochloric Acid → HCID 18648614, compound

HRID 1590362Notes

Reaction equation

HRID 1590362 reaction equation
CO.C(OC([NH:10][C@@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:17]=2)[CH2:12]1)=O)(C)(C)C.[ClH:28]>C(O)C>[ClH:28].[NH2:10][C@@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][CH:17]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10427900HCID 10427900, compound

Product 1

HCID 18648614HCID 18648614, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.5 g of (R)-2-tert-butoxycarbonylamino-7-carbethoxymethoxytetraline, EXAMPLE 3, in 35 ml of methylene chloride is cooled to 0° C. Then, there is added a solution of 7.7 ml of trifluoroacetic acid in 40 ml of methylene chloride and the mixture is left to stand under stirring at first 30 minutes at a temperature of 0°-5° C., then 4 hours at room temperature. After neutralization with a solution of sodium bicarbonate, the organic phase is separated, washed with water, dried and evaporated to dryness. The residue is taken up with 15 ml of ethyl acetate and made acid with a solution of hydrochloric acid in ethanol. The precipitated so obtained is filtered and washed with ether. Thus, 1.1 g of (R)-2-amino-7-carbethoxymethoxytetraline hydrochloride is obtained; m.p. 168°-171° C., /alpha/=+51.14° (methanol, c=1%). (b) To a solution of 5.8 g of (R)-2-tert-butoxycarbonylamino-7-carbethoxymethoxytetraline, EXAMPLE 3, in 135 ml of absolute ethanol there is added at room temperature 82 ml of a 7.2. N solution of hydrogen chloride in ethanol. The mixture is left under stirring at room temperature for 150 minutes, then it is evaporated to dryness under reduced pressure. The residue is taken up with ethyl ether and filtered. Thus, 4.6 g of (R)-2-amino-7-carbethoxymethoxytetraline hydrochloride are obtained; m.p. 170°-171° C., /alpha/=+51° (methanol, c=1%). By crystallization from methanol, the melting point remains unchanged (170°-172° C.) and the /alpha/ rises to +51.6° (methanol, c=1%).

Workup

  1. waitThe mixture is left
  2. customit is evaporated to dryness under reduced pressure
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2d3ddfd2d49b421e9de3163156b6df5c
Source dataset
uspto-grants-1993_04
Patent number
US05202466

Reaction notes

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