Sodium borohydride → HCID 89748270, compound

HRID 60776Notes

Reaction equation

HRID 60776 reaction equation
[BH4-].[Na+].[Br-].[CH2:4]([N+:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO.CCOC(C)=O>[CH2:4]([N:11]1[CH:16]=[C:15]([F:17])[CH2:14][CH2:13][CH:12]1[CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 897394131-Benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide

Product 1

HCID 89748270HCID 89748270, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaBH4 (5.56 mmol, 0.21 g) was added to a solution of 1-benzyl-2-((tert-butoxycarbonylamino)methyl)-5-fluoropyridinium bromide (1.40 mmol, 0.60 g) in MeOH at 0° C. The resulting mixture was stirred at 0° C. for 40 min. An aliquot was checked by analytical HPLC and some of the starting material remained. Additional NaBH4 (5.56 mmol, 0.21 g) was added at 0° C. and the resulting mixture was stirred for extra 40 min. The reaction mixture was diluted with EtOAc and washed with brine. EtOAc layer was separated, dried with MgSO4 and concentrated in vacuo to give desired tert-butyl (1-benzyl-5-fluoro-1,2,3,4-tetrahydropyridin-2-yl)methylcarbamate in 62% yield which was used for next step without further purification. MS (ESI) 321 (M+H).

Workup

  1. stirringthe resulting mixture was stirred for extra 40 min
  2. washwashed with brine
  3. customEtOAc layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-702c2305c8d94f92869c11bce1371cc2
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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