Sodium borohydride → Benzyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 336628Notes

Reaction equation

HRID 336628 reaction equation
[CH:1]([CH:3]1[CH2:9][CH:8]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:12])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)=[O:2].[BH4-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH:3]1[CH2:4][CH:5]2[N:10]([C:11]([O:13][CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:12])[CH:8]([CH2:7][CH2:6]2)[CH2:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 51030438Benzyl 3-formyl-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 53487624Benzyl 3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 84B (3.4 g) in tetrahydrofuran (40 mL) was added NaBH4 (0.5 g). The mixture was stirred overnight. The solvent was evaporated and the residue was added to ethyl acetate (300 mL) and water (50 mL). The organic layer was washed with water and brine, dried over Na2SO4, and filtered. Evaporation of the solvent gave the crude title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was added to ethyl acetate (300 mL) and water (50 mL)
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-575c2f2b01424569acc986c3345c6474
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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