Sodium borohydride → HCID 86695583, compound

HRID 1465718Notes

Reaction equation

HRID 1465718 reaction equation
[O:1]=[C:2]1[CH2:8][C@@H:7]2[N:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:4]([CH2:5][CH2:6]2)[CH:3]1[C:17]([O:19][CH3:20])=[O:18].[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:8][C@@H:7]2[N:9]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@@H:4]([CH2:5][CH2:6]2)[CH:3]1[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86695584HCID 86695584, compound

Product 1

HCID 86695583HCID 86695583, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,5R)-8-Tert-butyl 2-methyl 3-oxo-8-azabicyclo[3.2.1]octane-2,8-dicarboxylate (2 g, 7.04 mmol) was dissolved in MeOH (26 mL), sodium borohydride (280 mg, 7.39 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 1.5 hours. After evaporation, the crude mixture was dissolved in EtOAc, washed with saturated NaHCO3 and water. Dried and concentrate to give 1.75 g of crude product. The crude was carried over the next step without further purification.

Workup

  1. customAfter evaporation
  2. dissolutionthe crude mixture was dissolved in EtOAc
  3. washwashed with saturated NaHCO3 and water
  4. customDried
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-109bbaacc1ee40f392468371b3d68deb
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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