Sodium borohydride → HCID 86586719, compound

HRID 2088181Notes

Reaction equation

HRID 2088181 reaction equation
FC(F)(F)C1C=C(CO[C@@H]2CC[C@@H]3N[C@@]2(C2C=CC=CC=2)C[C@H]3C2N(CSC3C=CC=CC=3)N=NC=2)C=C(C(F)(F)F)C=1.[F:44][C:45]([F:86])([F:85])[C:46]1[CH:47]=[C:48]([CH2:56][O:57][C@@H:58]2[CH2:64][CH2:63][C@@H:62]3[NH:65][C@@:59]2([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:60][C@H:61]3[C:66]2[N:70]=[N:69][N:68]([CH2:71]SC3C=CC=CC=3)[CH:67]=2)[CH:49]=[C:50]([C:52]([F:55])([F:54])[F:53])[CH:51]=1.[BH4-].[Na+]>CO.C1COCC1.O.O.O.O.O.O.[Ni](Cl)Cl>[F:55][C:52]([F:53])([F:54])[C:50]1[CH:49]=[C:48]([CH2:56][O:57][C@@H:58]2[CH2:64][CH2:63][C@@H:62]3[NH:65][C@@:59]2([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[CH2:60][C@H:61]3[C:66]2[N:70]=[N:69][N:68]([CH3:71])[CH:67]=2)[CH:47]=[C:46]([C:45]([F:44])([F:85])[F:86])[CH:51]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 86586720HCID 86586720, compoundHCID 86586721HCID 86586721, compound

Product 1

HCID 86586719HCID 86586719, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1R*,2R*,5S*,6R*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-phenylthiomethyl-1,2,3-triazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane and (1R*,2R*,5S*,6R*)-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(3-phenylthiomethyl-1,2,3-triazol-5-yl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 100; 99 mg, 0.1 mmol) and nickel(II)chloride hexahydrate (233 mg, 1.0 mmol) in methanol (6 ml) and THF (2 ml) at 0° C. was treated with sodium borohydride (112 mg, 2.9 mmol). A black precipitate was formed and the mixture was stirred for 20 minutes. The mixture was filtered through Celite™ and the filtrate concentrated in vacuo. The isomers were separated by preparative TLC eluting with 1:1 ethyl acetate/hexane to afford the title compounds (3-methyl-1,2,3-triazol-5-yl isomer: 17 mg) and (1-methyl-1,2,3-triazol-5-yl isomer: 34 mg), in a combined yield of 61%.

Workup

  1. customA black precipitate was formed
  2. filtrationThe mixture was filtered through Celite™
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe isomers were separated by preparative TLC
  5. washeluting with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0217e0fe970c4764bccdf8170b1b20e6
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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