Cyclobutanone → HCID 67126394, compound

HRID 574910Notes

Reaction equation

HRID 574910 reaction equation
[CH:1]1([NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:17])=[O:16])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:3][CH2:2]1.[C:22]1(=O)[CH2:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:22]1([N:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:5][CH2:6][CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:18])(=[O:16])=[O:17])=[CH:11][C:10]=2[N+:19]([O-:21])=[O:20])[CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 43599637HCID 43599637, compound

Product 1

HCID 67126394HCID 67126394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of EXAMPLE 308A (314 mg) in dichloromethane (5 mL) was added cyclobutanone (70 mg) followed by sodium triacetoxyborohydride (318 mg). The mixture was stirred overnight. The mixture was diluted with dichloromethane (300 mL) and washed with aqueous NaHCO3, water and brine and dried over Na2SO4. After filtration, evaporation of solvent gave the title compound.

Workup

  1. washwashed with aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration, evaporation of solvent

Sources & evidence

ORD record
ord-4bd0396c5ca64a30b27a71f6cb9532fe
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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