Water → HCID 14950483, compound

HRID 1769072Notes

Reaction equation

HRID 1769072 reaction equation
[BH4-].[Li+].[CH3:3][C:4]1[C:9]([C:10]2C=CN=CC=2)=[C:8]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:30]3[N:31]=[N:32][N:33]([C:35]([C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)([C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[N:34]=3)=[CH:20][CH:19]=2)[CH:7]=[C:6]([CH3:54])[N:5]=1.[OH2:55]>O1CCCC1>[OH:55][CH2:10][C:9]1[C:4]([CH3:3])=[N:5][C:6]([CH3:54])=[CH:7][C:8]=1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]2[N:31]=[N:32][N:33]([C:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:34]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 18946463HCID 18946463, compound

Product 1

HCID 14950483HCID 14950483, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium borohydride (66 mg) was added over a period of 10 minutes to a solution of compound A (800 mg) in tetrahydrofuran (THF) (25 ml) stirred at 0° C. under an atmosphere of argon. The solution was then stirred at ambient temperature for 16 hours, cooled to 0° C. and water (100 ml) was added. The mixture was extracted with dichloromethane (2×50 ml) and the extracts were washed with saturated sodium chloride solution (50 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with methanol/dichloromethane (1:19 v/v, to give 3-hydroxymethyl-2,6-dimethyl-4-[(2'-(2-triphenylmethyl-2-H-tetrazol-5-yl)biphenyl-4-yl)methoxy]pyridine (B) (246 mg), as a foam; NMR (d6 -DMSO/d4 -acetic acid): 2.55(s,3H), 2.65(s,3H), 4.7(s,2H), 5.4(s,2H), 6.9-7.0(m,6H), 7.2(d,2H), 7.25-7.45(complex m,12 H), 7.45-7.8(complex m,3H), 7.9(dd,1H).

Workup

  1. stirringThe solution was then stirred at ambient temperature for 16 hours
  2. temperaturecooled to 0° C.
  3. extractionThe mixture was extracted with dichloromethane (2×50 ml)
  4. washthe extracts were washed with saturated sodium chloride solution (50 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue purified by flash chromatography
  8. washeluting with methanol/dichloromethane (1:19 v/v

Sources & evidence

ORD record
ord-a046cb8886394d72a225ec3445153abb
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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