Cyclopentanone → HCID 67187353, compound

HRID 735848Notes

Reaction equation

HRID 735848 reaction equation
[NH2:1][CH2:2][C:3]1[S:7][C:6]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:10])=[O:9])=[CH:5][CH:4]=1.[C:24]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25]1.C([BH3-])#N.[Na+]>CN(C=O)C>[CH:24]1([NH:1][CH2:2][C:3]2[S:7][C:6]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:9])=[O:10])=[CH:5][CH:4]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 67186603HCID 67186603, compound

Product 1

HCID 67187353HCID 67187353, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The resin-bound 5-(aminomethyl)-N-dodecylthiophene-2-sulfonamide (example 125, step c, 0.23 mmol) was swelled in a 1% HAc in DMF mixture for 15 min at rt Cyclopentanone (97 mg, 1.15 mmol) and sodium cyanoborohydride (144 mg, 2.3 mmol) were then added and the reaction mixture shaken 14 h at rt. The resin was washed successively with DMF (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min). The resin was then dried under vacuum to afford the title compound which was used directly in the next step.

Workup

  1. washThe resin was washed successively with DMF (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min)
  2. customThe resin was then dried under vacuum

Sources & evidence

ORD record
ord-a2c2922ecc5a4ce5a41bc106ddb5d1c7
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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