Trifluoroacetic acid → HCID 58966608, compound

HRID 1674724Notes

Reaction equation

HRID 1674724 reaction equation
[C:1]([NH:4][C@@H:5]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]2([CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[NH:11]1[CH2:12][CH2:13][C:8]2([C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7]2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58033730HCID 58033730, compound

Product 1

HCID 58966608HCID 58966608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., a solution of (B4) (2.2 g, 6.1 mmol) in dichloromethane (20 ml) was treated with TFA (10 ml) for 1 hour, concentrated, co-evaporated with acetonitrile and dissolved in dichloromethane. The resulting solution washed with a mixture of brine (ca. 100 ml) and 6N NaOH (3 ml), dried over Na2SO4 and concentrated to give (S)-N-(3,4-dihydro-2H -spiro[naphthalene-1,4′-piperidine]-4-yl)acetamide (B5) as a white solid. LC-MS: m/e=258.9 (M+H). Rt=0.96 min. The crude was used directly for further reactions.

Workup

  1. concentrationconcentrated, co-evaporated with acetonitrile
  2. dissolutiondissolved in dichloromethane
  3. washThe resulting solution washed with a mixture of brine (ca. 100 ml) and 6N NaOH (3 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ac862c85652f4cc59b9d8688b226e30a
Source dataset
uspto-grants-2011_08
Patent number
US08003660B2

Reaction notes

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