Sodium borohydride → HCID 70171855, compound

HRID 2306264Notes

Reaction equation

HRID 2306264 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=S)[CH2:15][C:16]2[N:17]=[CH:18][N:19]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][C:16]2[N:17]=[CH:18][N:19]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 88190249HCID 88190249, compound

Product 1

HCID 70171855HCID 70171855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-N-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]-2-[1-(triphenylmethyl)-1H-imidazol-4-yl]thioacetamide, as described above in Step D, 1.29 g, 2.33 mmol) in TBF (65 mL) and MeOH (65 mL), was added NiCl2.6H2O (2.22 g, 9.33 mmol). The mixture was cooled to 0° C. and NaBH4 (2 M in THF, 4.7 mL, 9.33 mmol) was slowly added. After 30 min, the solvent was partially removed in vacuo, and the residual mixture was partitioned between saturated aqueous Na2CO3 containing NH4OH and Et2O. The organic layer was removed and the aqueous layer was further extracted with EtOAc (2×). The combined organic extracts were combined, dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of CH2Cl2—1% to 10% MeOH—0.1% to 1% NH4OH, to yield the above-titled compound.

Workup

  1. customthe solvent was partially removed in vacuo
  2. customthe residual mixture was partitioned between saturated aqueous Na2CO3
  3. additioncontaining NH4OH and Et2O
  4. customThe organic layer was removed
  5. extractionthe aqueous layer was further extracted with EtOAc (2×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel
  10. washeluting with a gradient of CH2Cl2—1% to 10% MeOH—0.1% to 1% NH4OH

Sources & evidence

ORD record
ord-c72fe2c07c37436a903150b92f94ff74
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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