Sodium borohydride → HCID 59394969, compound

HRID 1465089Notes

Reaction equation

HRID 1465089 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]([F: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]([F: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 59395072HCID 59395072, compound

Product 1

HCID 59394969HCID 59394969, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyclopentyl-4-fluoro-5-nitrophenyl methyl carbonate (2022 mg, 7.14 mmol) and NiCl2 (925 mg, 7.14 mmol) in methanol (10 mL) cooled to 0° C. was added NaBH4 (810 mg, 21.42 mmol) portion-wise. The reaction was stirred for 10 min then quenched with NaHCO3. The mixture was diluted with ethyl acetate and filtered through a pad of Celite. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (10% ethyl acetate/hexanes) provided 5-amino-2-cyclopentyl-4-fluorophenyl methyl carbonate (1232 mg, 68% yield) as brown solid. 1H NMR (400.0 MHz, DMSO-d6) δ 6.94 (d, J=12.6 Hz, 1H), 6.50 (d, J=8.2 Hz, 1H), 5.17 (s, 2H), 3.81 (s, 3H), 2.84 (dd, J=8.4, 17.2 Hz, 1H), 1.87-1.80 (m, 2H), 1.75-1.67 (m, 2H), 1.62-1.53 (m, 2H), 1.45-1.36 (m, 2H). MS (ESI) m/z (M+H+): 255.1.

Workup

  1. customthen quenched with NaHCO3
  2. additionThe mixture was diluted with ethyl acetate
  3. filtrationfiltered through a pad of Celite
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-37a6260a77b44552b98a6f8c7d6cf30b
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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