Lithium borohydride → Biphenyl-2-yl(2-(hydroxymethyl)-5,5-dimethoxypiperidin-1-yl)methanone

HRID 60811Notes

Reaction equation

HRID 60811 reaction equation
C1(C2C=CC=CC=2)C(C(N2CC(=O)CCC2C(OC)=O)=O)=CC=CC=1.[C:26]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:27]([C:32]([N:34]2[CH2:39][C:38]([O:42][CH3:43])([O:40][CH3:41])[CH2:37][CH2:36][CH:35]2[C:44](OC)=[O:45])=[O:33])=[CH:28][CH:29]=[CH:30][CH:31]=1.[Li+].[BH4-]>C1COCC1>[C:26]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]([N:34]1[CH2:39][C:38]([O:40][CH3:41])([O:42][CH3:43])[CH2:37][CH2:36][CH:35]1[CH2:44][OH:45])=[O:33]

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 89739342Methyl 1-(biphenylcarbonyl)-5,5-dimethoxypiperidine-2-carboxylateHCID 89739424Methyl 1-(biphenylcarbonyl)-5-oxopiperidine-2-carboxylate

Product 1

HCID 89739772Biphenyl-2-yl(2-(hydroxymethyl)-5,5-dimethoxypiperidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-(biphenylcarbonyl)-5-oxopiperidine-2-carboxylate was converted to methyl 1-(biphenylcarbonyl)-5,5-dimethoxypiperidine-2-carboxylate (4.3 mmol, 1.65 g) following the general protocol described in Part I above. To a solution of this ketal in anhydrous THF was added LiBH4 (2M in THF) (9.4 mmol, 4.7 mL) at 0° C. under argon. The resulting mixture was stirred at rt and the reaction was tracked by analytical HPLC. The reaction was carefully quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was separated, dried with MgSO4, and concentrated in vacuo to give desired biphenyl-2-yl(2-(hydroxymethyl)-5,5-dimethoxypiperidin-1-yl)methanone in quantitative yield which was used for next step without further purification.

Workup

  1. customThe reaction was carefully quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-faf1471695524c8583a03d25b2ed6a36
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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