Acetate → HCID 12732179, compound

HRID 555810Notes

Reaction equation

HRID 555810 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:16])([CH3:15])[CH3:14])C1C=CC=CC=1.CC1C=C2N=C3C(=NC(NC3=O)=O)N(C[C@H](O)[C@H](O)[C@H](O)CO)C2=CC=1C.CC([O-])=O>CO>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 175AcetateHCID 493570RiboflavinHCID 10554200HCID 10554200, compound

Product 1

HCID 12732179HCID 12732179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(1-benzylpyrrolidin-2-yl)propan-2-ol (1.38 g, 6.29 mmol) in MeOH (50 mL) was added palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet, degussa type e101 ne/w (230 mg, 1.64 mmol) and acetic acid glacial (690 μl, 12.0 mmol). The reaction mixture was stirred at RT under 1 atm of H2 for 24 h. The reaction mixture was filtered through a pad of celite and washed with MeOH. The solvent was evaporated and the residue was partitioned between 2 N NaOH and EtOAc. The aqueous layer was extracted with EtOAc (2×) and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 50% to 100% MeOH in EtOAc, to provide (S)-2-(pyrrolidin-2-yl)propan-2-ol as an orange oil.

Workup

  1. dry with materialpalladium hydroxide, 20 wt % pd (dry basis) on carbon
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed with MeOH
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between 2 N NaOH and EtOAc
  6. extractionThe aqueous layer was extracted with EtOAc (2×)
  7. dry with materialthe combined organic layer was dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
  10. washeluting with a gradient of 50% to 100% MeOH in EtOAc

Sources & evidence

ORD record
ord-44bc77f5876144099f7303759894e513
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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