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Sodium triacetoxyborohydride → 4-([Methyl-(2-pyridin-4-ylpyrimidin-4-ylmethyl)amino]methyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 1921913
Notes
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Reaction equation

HRID 1921913 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:28]=[C:27]([CH:29]=O)[CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:16])[CH2:29][C:27]2[CH:26]=[CH:25][N:24]=[C:23]([C:20]3[CH:19]=[CH:18][N:17]=[CH:22][CH:21]=3)[N:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylateHCID 534417682-Pyridin-4-YL-pyrimidine-4-carbaldehyde

Product 1

HCID 115603394-([Methyl-(2-pyridin-4-ylpyrimidin-4-ylmethyl)amino]methyl}piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 4-methylaminomethylpiperidine-1-carboxylic acid tert-butyl ester (37 mg, 0.16 mmol) in anhydrous CH2Cl2 (3 mL) was added 2-pyridin-4-yl-pyrimidine-4-carbaldehyde (Preparation 2, 30 mg, 0.16 mmol) followed by NaBH(OAc)3 (38 mg, 0.18 mmol). The mixture was stirred vigorously at rt for 24 h, before being partitioned between CH2Cl2 (30 mL) and H2O (20 mL). The aqueous phase was extracted with CH2Cl2 (20 mL), then the combined organics were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (EtOAc) gave the title compound. RT=2.36 min; m/z (ES+)=398 [M+H]+.

Workup

  1. custombefore being partitioned between CH2Cl2 (30 mL) and H2O (20 mL)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (20 mL)
  3. washthe combined organics were washed with brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4428db75a4794b72a76bd77038264b5e
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173807B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes