Dimethylformamide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 2194941Notes

Reaction equation

HRID 2194941 reaction equation
C(=O)([O-])[O-].[K+].[K+].ClC([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.C(OCC)(=O)C.[CH3:23][CH2:24][CH2:25][CH2:26]CC.C[N:30](C=O)C>>[NH2:30][C:26]1[CH:25]=[CH:24][CH:23]=[C:14]2[C:15]=1[CH2:16][C@H:11]([OH:10])[CH2:12][CH2:13]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 21226206Ethyl acetate hexane

Product 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenolYield 53%

Conditions

Temperature
0 °C

Procedure

To a stirred solution of stage-c product (5 g, 0.026 mol) in DMF (25 ml, 5 times), potassium carbonate (12.64 g, 0.09 mol, 3.5 eq) was added. Cooled the contents to 0° C., phenyl chloroformate (4.5 g (3.63 ml), 0.023 mol) was added drop wise and stirred the contents for 15-20 min. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.5). On completion of the reaction, filtered the contents and washed with ethyl acetate (100 ml). Filtrate was taken in cold water (150 ml), organic layer was separated and dried over sodium sulfate. The solvent removed under reduced pressure and the crude obtained was purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to yield the titled product as a pale yellow colored solid (4.3 g, 53% yield, mp 142-144° C.).

Workup

  1. customOn completion of the reaction
  2. filtrationfiltered the contents
  3. washwashed with ethyl acetate (100 ml)
  4. customorganic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThe solvent removed under reduced pressure
  7. customthe crude obtained
  8. customwas purified by column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7be2205c9cba437e90ec19cee705a031
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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