Sodium borohydride → Tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate

HRID 81123Notes

Reaction equation

HRID 81123 reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]2[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]1[CH2:4][CH2:5]2.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH:6]2[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:3]1[CH2:4][CH2:5]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15240743tert-Butyl 2-oxo-7-azabicyclo(2.2.1)heptane-7-carboxylate

Product 1

HCID 21188409Tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate (500 mg, 2.37 mmol) in methanol (4.7 mL) at 0° C. was added sodium borohydride (134 mg, 3.55 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then stirred for 16 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride and concentrated. The resulting residue was extracted with DCM (3×) and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford tert-butyl 2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate. 1H NMR (500 MHz, CDCl3) δ 4.35 (broad, 1H), 4.13 (s, 2H), 2.28-2.19 (m, 1H), 2.18-2.12 (m, 1H), 1.83-1.75 (m, 1H), 1.71-1.68 (m, 1H), 1.66-1.56 (m, 1H), 1.56-1.48 (m, 1H), 1.44 (s, 9H), 1.05 (dd, J=3.4, 12.7, 1H).

Workup

  1. stirringstirred for 16 hours at room temperature
  2. customThe mixture was quenched with saturated aqueous ammonium chloride
  3. concentrationconcentrated
  4. extractionThe resulting residue was extracted with DCM (3×)
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cecb41a023c34f3fbb7ab42826041b8c
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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