Sodium borohydride → HCID 59394973, compound

HRID 383336Notes

Reaction equation

HRID 383336 reaction equation
[C:1](=[O:20])([O:18][CH3:19])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([Cl:12])=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[BH4-].[Na+]>CO.Cl[Ni]Cl>[C:1](=[O:20])([O:18][CH3:19])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([Cl:12])=[CH:5][C:4]=1[CH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59394942HCID 59394942, compound

Product 1

HCID 59394973HCID 59394973, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-chloro-2-cyclopentyl-5-nitrophenyl methyl carbonate (870 mg, 2.90 mmol) and NiCl2 (376 mg, 2.90 mmol) in methanol (10 mL) at 0° C. was added NaBH4 (330 mg, 8.71 mmol) portion-wise. After 10 min the reaction was quenched with NaHCO3 and diluted with ethyl acetate. The reaction mixture was filtered through a pad of Celite and the layers were separated. The aqueous layer was re-extracted with ethyl acetate (3×100 mL) and the combined organic extracts dried over MgSO4. The solution was filtered and concentrated in vacuo to provide 5-amino-4-chloro-2-cyclopentylphenyl methyl carbonate which was used for the next step without further purification (400 mg, 51% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.11 (s, 1H), 6.57 (d, J=11.4 Hz, 1H), 5.38 (s, 1H), 3.85-3.80 (m, 3H), 2.89-2.80 (m, 2H), 1.88-1.81 (m, 2H), 1.75-1.56 (m, 2H), 1.52 (s, 2H), 1.46-1.37 (m, 2H).

Workup

  1. customAfter 10 min the reaction was quenched with NaHCO3
  2. additiondiluted with ethyl acetate
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. customthe layers were separated
  5. extractionThe aqueous layer was re-extracted with ethyl acetate (3×100 mL)
  6. dry with materialthe combined organic extracts dried over MgSO4
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61be7309704243a5bbd314811fa29448
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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