Tetrahydrofuran → 2-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol

HRID 709844Notes

Reaction equation

HRID 709844 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[NH2:12][C:13]([CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=2)[CH2:21]1)([CH3:19])[C:14](OCC)=[O:15]>C(OCC)(=O)C>[NH2:12][C:13]([CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=2)[CH2:21]1)([CH3:19])[CH2:14][OH:15]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 67422105Ethyl 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate

Product 1

HCID 461946762-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-olYield 49.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a 2 L flask cooled by ice water was added 60 g LiAlH4, and 1 L of THF. When the mixture was cooled to below 10° C., a mixture of 118.8 grams of ethyl 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate and 350 mL THF was added dropwise. No starting material remained by HPLC. The temperature was kept below 30° C. while 100 mL ethyl acetate was added. To the concentrated mixture was added 400 mL ethyl acetate, followed by 25 mL ice water. The mixture was filtered, and the filter cake with 300 mL ethyl acetate. The combined organic layers washed with brine 100 mL×2, dried with Na2SO4, decolorized with carbon and concentrated. To the oil, was added ether, the mixture stirred for overnight, filtered and dried to afford 50 g of 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol.

Workup

  1. temperatureWhen the mixture was cooled to below 10° C.
  2. additionwas added dropwise
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. washThe combined organic layers washed with brine 100 mL×2
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. additionTo the oil, was added ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-37d7a537d71d49f2a075237214b9bd62
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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