Sodium borohydride → 2-Benzyl-5-methoxy-1,2,3,3a,8,8a-hexahydro-2-aza-cyclopenta[a]inden-8-ol

HRID 508522Notes

Reaction equation

HRID 508522 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:24][CH:13]2[C:14]3[CH:15]=[C:16]([O:22][CH3:23])[CH:17]=[CH:18][C:19]=3[C:20](=[O:21])[CH:12]2[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:24][CH:13]2[C:14]3[CH:15]=[C:16]([O:22][CH3:23])[CH:17]=[CH:18][C:19]=3[CH:20]([OH:21])[CH:12]2[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672034582-Benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one

Product 1

HCID 672032982-Benzyl-5-methoxy-1,2,3,3a,8,8a-hexahydro-2-aza-cyclopenta[a]inden-8-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (0.27 g, 6.8 mmol) was added to a solution of 2-benzyl-5-methoxy-2,3,3a,8a-tetrahydro-1H-2-aza-cyclopenta[a]inden-8-one (from Example 1, Step C) (1.0 g, 3.4 mmol) in MeOH (17 mL), and stirred for 2 hours at room temperature. The reaction solution was concentrated via rotary evaporation and the residue dissolved in EtOAc. The organic solution was washed with a saturated aqueous NaHCO3 solution and brine, dried over MgSO4, and concentrated. The crude product was obtained without further purification. MS calculated for C19H21NO2+H: 296, observed: 296.

Workup

  1. concentrationThe reaction solution was concentrated via rotary evaporation
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic solution was washed with a saturated aqueous NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-885b3bf7fd79447ba2b31fd8a9dccc94
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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