Sodium borohydride → 543713-48-0

HRID 2111676Notes

Reaction equation

HRID 2111676 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1)=O)C>C(O)C>[OH:5][CH2:6][C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10588096Ethyl 5-(N-Boc)aminomethylisoxazole-3-carboxylate

Product 1

HCID 67284568543713-48-0Yield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (610 mg, 16 mmol) was added in portions to a solution of 3-ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 1.62 g, 6 mmol) in ethanol (15 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 hours then quenched with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with EtOAc and the organics washed with brine then dried (MgSO4). The solvent was removed by evaporation to give the title compound (1.25 g, 91%). NMR (DMSO): 1.38 (s, 9H), 4.21 (d, 2H), 4.44 (s, 2H), 5.40 (br s, 1H), 6.21 (s, 1H), 7.49 (br s, 1H); m/z 229 (MH)+.

Workup

  1. customthen quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organics washed with brine
  4. dry with materialthen dried (MgSO4)
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-07fe8723aa004bea94974bd30ed18511
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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