Lithium borohydride → HCID 69672941, compound

HRID 1426345Notes

Reaction equation

HRID 1426345 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([C:22](OC)=[O:23])[CH:21]=1)[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.[BH4-].[Li+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([CH2:22][OH:23])[CH:21]=1)[O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69673538HCID 69673538, compound

Product 1

HCID 69672941HCID 69672941, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-[3-bromo-5-(methoxycarbonyl)phenoxy]piperidine-1-carboxylate (520 mg, 1.2 mmol) in THF (10 mL) was added lithium tetrahydroborate (27.3 mg, 1.26 mmol). The resulting solution was stirred at room temperature for 1 hour. The reaction was quenched with 1N HCl. The organic solution was washed with brine, dried over Na2SC4, filtered and concentrated. The crude was purified by flash chromatography on a silica gel column to give the desired product. LCMS (M+Na)+: 408.1, 410.1.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. washThe organic solution was washed with brine
  3. dry with materialdried over Na2SC4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-f996f835772342589fec12f428d7f2e5
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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