Hydrochloric Acid → rac-(2R,3R)-3-amino-1,2,3,4-tetrahydronaphthalen-2-ol hydrochloride

HRID 2249103Notes

Reaction equation

HRID 2249103 reaction equation
C1(C(C)C([CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH:12]([NH2:20])[C@@H:11]2[OH:21])=O)C=CC=CC=1.[ClH:23]>>[ClH:23].[NH2:20][C@@H:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C@H:11]1[OH:21]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131716987(2R)-2-phenylpropanoyl-3-amino-1,2,3,4-tetrahydro-2-naphthalenol

Product 1

HCID 12878372rac-(2R,3R)-3-amino-1,2,3,4-tetrahydronaphthalen-2-ol hydrochloride

Procedure

Trans-N-[(2R)-2-phenylpropanoyl-3-amino-1,2,3,4-tetrahydro-2-naphthalenol, diastereoisomer A (183 mg) was refluxed in 6N aqueous hydrochloric acid (20 ml) for 4 hours. The reaction mixture was evaporated in vacuo and the residue taken up in water. The aqueous solution was washed with ethyl acetate and evaporated to give a white solid which was recrystallized from a methanol/ethyl acetate mixture to yield the title compound (99 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. washThe aqueous solution was washed with ethyl acetate
  3. customevaporated
  4. customto give a white solid which
  5. customwas recrystallized from a methanol/ethyl acetate mixture

Sources & evidence

ORD record
ord-9f44803df933400cafc1951e0ce8d83a
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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