Sodium borohydride → t-Butyl {2-[4-(3-hydroxy-propenyl)-benzoylamino]-phenyl}-carbamate

HRID 1180809Notes

Reaction equation

HRID 1180809 reaction equation
[O:1]=[CH:2][CH:3]=[CH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])=[CH:7][CH:6]=1.[BH4-].[Na+]>C(O)C>[OH:1][CH2:2][CH:3]=[CH:4][C:5]1[CH:27]=[CH:26][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 72479807t-Butyl {2-[4-(3-oxo-propenyl)-benzoylamino]-phenyl}-carbamate

Product 1

HCID 72479808t-Butyl {2-[4-(3-hydroxy-propenyl)-benzoylamino]-phenyl}-carbamateYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of compound XVI (1.00 g, 2.79 mmol) in ethanol (15 ml) under nitrogen was added sodium borohydride (110 mg, 2.73 mmol). After 5 min, the reaction mixture was quenched with water and diluted with AcOEt. After separation the organic layer was successively washed with brine, dried over MgSO4, filtered, and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60) to afford the title compound XVIII (910 mg, 2.29 mmol, 82% yield) as a pale yellow solid (slightly contaminated with the diene). 1H NMR (300 MHz, CDCl3) δ(ppm): 9.20 (s, 1H), 7.90 (d, J=7.8 Hz, 2H), 7.75 (d, J=7.5 Hz, 1H), 7.43 (d, J=8.4 Hz, 2H), 7.32–7.08 (m, 3H), 6.94 (s, 1H), 6.65 (d, J=15.9 Hz, 1H), 6.45 (td, J=15.9, 5.4 Hz, 1H), 4.35 (d, J=5.4 Hz, 2H), 1.92 (s, 1H), 1.51 (s, 9H).

Workup

  1. customthe reaction mixture was quenched with water
  2. additiondiluted with AcOEt
  3. customAfter separation the organic layer
  4. washwas successively washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60)

Sources & evidence

ORD record
ord-9c903c99d2514b87a87a219a69da7436
Source dataset
uspto-grants-2007_10
Patent number
US07282608B2

Reaction notes

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