Sodium Hydroxide → (1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 75573Notes

Reaction equation

HRID 75573 reaction equation
FC(F)(F)C([NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([OH:16])[CH2:8][CH2:7]1)=O.[OH-].[Na+]>CO.O.C(Cl)Cl>[NH2:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:9]([OH:16])[CH2:8][CH2:7]1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 866866812,2,2-Trifluoro-N-((1S,4S)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide

Product 1

HCID 86686682(1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-olYield 84%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a grey solution of Intermediate 5a (5.55 g, 21.4 mmol) in MeOH (50 mL), NaOH (1.28 g, 32.1 mmol) in water (15 mL) was added, and the mixture stirred at room temperature for 3 days. NaOH (1.28 g, 32.1 mmol) was further added and the brown solution was stirred for 5 h. The solution was applied directly to an SCX-2 column, washing with MeOH and eluting with 2M NH3 in MeOH, and concentrated under vacuum to leave a grey solid. The solid was suspended in DCM (50 mL) with sonication, then filtered and dried under vacuum to leave a pale grey solid (2.93 g, 84%). 1H NMR (400 MHz, d6-DMSO): 1.41-1.64 (2H, m), 2.02-2.13 (2H, m), 3.82 (1H, dd), 4.55 (1H, dd), 5.08 (1H, br s), 7.13-7.22 (2H, m), 7.35-7.49 (2H, m).

Workup

  1. stirringthe brown solution was stirred for 5 h
  2. washwashing with MeOH
  3. washeluting with 2M NH3 in MeOH
  4. concentrationconcentrated under vacuum
  5. customto leave a grey solid
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ed14a9aea74d4ab5baf09a3b4fdae905
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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