Sodium cyanoborohydride → HCID 86694484, compound

HRID 1519615Notes

Reaction equation

HRID 1519615 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH:12]=O)=[CH:10][C:5]=2[CH2:4][O:3]1.[F:14][C:15]([F:30])([F:29])[CH:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.C([BH3-])#N.[Na+]>CO>[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:21]3[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:17][CH:16]3[C:15]([F:29])([F:14])[F:30])=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 665998503-Trifluoromethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 772312612-(1-Oxo-1,3-dihydroisobenzofuran-5-yl)acetaldehyde

Product 1

HCID 86694484HCID 86694484, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (0.495 g, 2.8 mmol) and tert-butyl 3-(trifluoromethyl)piperazine-1-carboxylate (0.65 g, 2.6 mmol) in methanol (5 ml) at 0° C. was added sodium cyanoborohydride (0.21 g, 3.3 mmol) and the reaction stirred 12 hours at RT. The reaction mixture was concentrated and diluted with water. The aqueous was extracted with dichloromethane and the combined organics washed with brine, dried (MgSO4), filtered and concentrated. MPLC chromatography (2→20% EtOAc:hexane) provided tert-butyl 4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-3-(trifluoromethyl)piperazine-1-carboxylate. LC-MS (IE, m/z): 415.1 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionThe aqueous was extracted with dichloromethane
  4. washthe combined organics washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5cb5b37da25f4e84a4ecea919691356e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

Loading…