Dichloromethane → HCID 18648614, compound

HRID 467318Notes

Reaction equation

HRID 467318 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:34]>>[ClH:34].[NH2:8][C@@H:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:14][CH:15]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 6422Trifluoroacetic acidHCID 10427900HCID 10427900, compound

Product 1

HCID 18648614HCID 18648614, compound

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 7.2N 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. custom4 hours
  3. customat room temperature
  4. customAfter neutralization with a solution of sodium bicarbonate, the organic phase is separated
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe precipitated so
  9. customobtained
  10. filtrationis filtered
  11. washwashed with ether

Sources & evidence

ORD record
ord-cda96ef51560488da1f0b9d79e030556
Source dataset
uspto-grants-1992_10
Patent number
US05159103

Reaction notes

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