Methanol → HCID 58442837, compound

HRID 41628Notes

Reaction equation

HRID 41628 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C:7]1[C:8]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1)=O.CO>C1COCC1.CCOC(C)=O>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([C:8]2[C:7]([CH2:5][OH:4])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58442811HCID 58442811, compound

Product 1

HCID 58442837HCID 58442837, compoundYield 44.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

NaBH4 (0.6 g, 15.8 mmol, 5 eq.) was added to a solution of 3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-3,1′-dicarboxylic acid 1′-t-butyl ester 3-methyl ester (1.0 g, 3.1 mmol, 1.0 eq.) in THF (40 mL), under nitrogen. This mixture was cooled to 0-5° C. and MeOH (8 mL) was added dropwise. The resulting solution was stirred for 2.5 hours at room temperature. The solution was diluted with EtOAc (50 mL), then washed with saturated NH4Cl (1×100 mL) and saturated aqueous NaCl (2×100 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with EtOAc/PE (1:5) to yield 3-hydroxymethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,4]-bipyridinyl-1′-carboxylic acid t-butyl ester (0.4 g) as a white solid. MS m/z: [M+H]+ calcd for C16H25N2O3, 293. found 293.

Workup

  1. washwashed with saturated NH4Cl (1×100 mL) and saturated aqueous NaCl (2×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under vacuum
  4. washeluted with EtOAc/PE (1:5)

Sources & evidence

ORD record
ord-54bc7f66c69e487e899b1b7f066e785c
Source dataset
uspto-grants-2013_09
Patent number
US08530663B2

Reaction notes

Loading…