Sodium Hydroxide → (1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octane

HRID 1267901Notes

Reaction equation

HRID 1267901 reaction equation
[CH2:1]([NH:8][C@H:9]1[C@@H:15]([F:16])[CH2:14][C@@H:13]2[N:17]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@:10]1([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:11][C@H:12]2[C:25](OC(C)(C)C)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH-](CC)CC)C.[Li+].[OH-].[Na+]>O1CCCC1>[CH2:1]([NH:8][C@H:9]1[C@@H:15]([F:16])[CH2:14][C@@H:13]2[N:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@:10]1([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:11][C@H:12]2[CH2:25][OH:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23664628LithiumtriethylborohydrideHCID 70008795HCID 70008795, compound

Product 1

HCID 70008699(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(hydroxymethyl)-8-azabicyclo[3.2.1]octaneYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(1R*,2R*,3S*,5S*,6R*)-2-Benzylamino-8-benzyl-3-fluoro-1-phenyl-6-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane (Description 36b; 651 mg, 1.3 mmol) was dissolved in tetrahydrofuran (10 mL) and then treated with a solution of lithium triethylborohydride in tetrahydrofuran (4 mL, 1M, 4 mmol). The solution was stirred at room temperature for 1 hour, then poured into aqueous sodium hydroxide solution (50 mL, 1M). The suspension formed was extracted with ethyl acetate (2×100 mL) and the extracts were dried (MgSO4). Concentration in vacuo gave a gum which was purified by silica chromatography to give the title compound (476 mg, 1.1 mmol).

Workup

  1. customThe suspension formed
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. dry with materialthe extracts were dried (MgSO4)
  4. concentrationConcentration in vacuo
  5. customgave a gum which
  6. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-9f87c07105784af785c7ce2dd3ddac50
Source dataset
uspto-grants-2003_04
Patent number
US06555552B2

Reaction notes

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