Sodium borohydride → HCID 58933788, compound

HRID 854325Notes

Reaction equation

HRID 854325 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[O:19])[CH2:14][CH2:13]1)=[O:9])=O.[BH4-].[Na+]>CO>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([CH:29]=[CH:30][CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[O:19])[CH2:16][CH2:17]1)=[O:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58933557HCID 58933557, compound

Product 1

HCID 58933788HCID 58933788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methylbenzyl 4-({[3-(methoxycarbonyl)benzoyl]amino}methyl)piperidine-1-carboxylate (EXAMPLE 540) (100 mg, 0.24 mmol) in MeOH (2 mL) was added sodium borohydride (0.18 mg, 4.7 mmol). The solution was stirred at rt for 2 h, quenched with saturated NH4Cl (aq) and extracted with EtOAc. The organic layer was dried over NaSO4, filtered and concentrated. The residue was chromatographed on silica gel (gradient elution, 2:1 hexane:EtOAc to EtOAc) to give 4-methylbenzyl 4-({[3-(hydroxymethyl)benzoyl]amino}methyl)piperidine-1-carboxylate.

Workup

  1. customquenched with saturated NH4Cl (aq)
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (gradient elution, 2:1 hexane:EtOAc to EtOAc)

Sources & evidence

ORD record
ord-5259ce19a7e34925a6c3e2821fe67ecb
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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