Sodium triacetoxyborohydride → Phthalide

HRID 2173447Notes

Reaction equation

HRID 2173447 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9](C(C)C=O)=[CH:10][C:5]=2[CH2:4][O:3]1.N1(C(=O)CC2C=CC(N3C=NN=N3)=CC=2)CCNCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:2]1(=[O:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67517237HCID 67517237, compoundHCID 77230676HCID 77230676, compound

Product 1

HCID 6885Phthalide

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolved 2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl) propanal (38 mg, 0.2 mmol) in dichloroethane (10 mL) and added 1-(piperazin-1-yl) 2-[4-(1H-tetrazol-1yl)phenyl]ethanone (50.1 mg, 0.162 mmol) followed by sodium triacetoxyborohydride (127 mg, 0.599 mmol) then stirred at room temperature for 16 h. The reaction mixture was washed with saturated NaHCO3 solution, brine, dried and concentrated. Purified by MPLC using a 40 g ISCO Redi-sep column and eluted with 0%-10% methanol/ethyl acetate to yield racemate 5-[1-4-{[4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)propan-2-yl]-2-benzofuran-1(3H)-one. The isomers were separated on Chiracel OD, 2 cm×25 cm, 10μ column using 45% ethanol: 55% heptane solvent system. The retention times for isomer A was at 42 minutes and for isomer B was at 47 minutes.

Workup

  1. washThe reaction mixture was washed with saturated NaHCO3 solution, brine
  2. customdried
  3. concentrationconcentrated
  4. customPurified by MPLC
  5. washeluted with 0%-10% methanol/ethyl acetate

Sources & evidence

ORD record
ord-1ea7155c726343b9931a9c2257827309
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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