Sodium borohydride → HCID 86587889, compound

HRID 1244079Notes

Reaction equation

HRID 1244079 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([CH3:16])([CH3:15])[CH2:9][CH:10]=[CH:11][N+:12]([O-:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][CH2:11][N+:12]([O-:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 73740413(1,1-Dimethyl-4-nitro-but-3-enyl)-carbamic acid tert-butyl ester

Product 1

HCID 86587889HCID 86587889, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (1,1-Dimethyl-4-nitro-but-3-enyl)-carbamic acid tert-butyl ester (2.0 g, 8.2 mmol) in 20 mL of EtOH was added NaBH4 (500 mg, 13.5 mmol). The mixture was stirred 1 h and then quenched with saturated NH4Cl (40 mL). The solution was extracted with EtOAc (2×25 mL), the extracts were washed with brine, dried with MgSO4 and concentrated. Silica gel chromatography (10:1 hexane/EtOAc) gave 1.57 g (78%) of a colorless oil: mass spectru m/e=147 (M−100).

Workup

  1. customquenched with saturated NH4Cl (40 mL)
  2. extractionThe solution was extracted with EtOAc (2×25 mL)
  3. washthe extracts were washed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b159b57dcb014f4798d546f1db26478a
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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