Lithium borohydride → HCID 67111267, compound

HRID 537369Notes

Reaction equation

HRID 537369 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:11]([C:22](OC)=[O:23])[CH2:10]1.[Li+].[BH4-]>C1COCC1.CO>[OH:23][CH2:22][CH:11]1[CH2:10][CH:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][CH2:13][N:12]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 67111285HCID 67111285, compound

Product 1

HCID 67111267HCID 67111267, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a solution of 1-tert-butyl 2-methyl 4-(2-methoxyphenyl)piperidine-1,2-dicarboxylate 124 (640 mg, 1.83 mmol) in THF (10 mL) and MeOH (0.5 mL), LiBH4 (60 mg, 2.74 mmol) was added. The reaction solution was stirred at r.t overnight, The reaction was quenched with water and the mixture was extracted with ethyl acetate. After removal of solvent, the crude product of tert-butyl 2-(hydroxymethyl)-4-(2-methoxyphenyl)piperidine-1-carboxylate 125 was obtained without further purification. LC/MS RT (5 min method)=2.027 min. Mass observed: 222.2 (M-Boc+H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. customAfter removal of solvent

Sources & evidence

ORD record
ord-5b55b4a12f7a4863b90427e18439b877
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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