Sodium Hydroxide → HCID 20737859, compound

HRID 354422Notes

Reaction equation

HRID 354422 reaction equation
[C:1]([N:8]1[C@H:12]([CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][C@H:9]1[CH2:22][O:23]C(=O)C1C=CC=CC=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([N:8]1[C@H:9]([CH2:22][OH:23])[CH2:10][CH2:11][C@H:12]1[CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20737856HCID 20737856, compound

Product 1

HCID 20737859HCID 20737859, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-Boc-2-(S)-benzoyloxymethyl-5-(S)-benzyloxymethylpyrrolidine (1.23 g, 2.89 mmol) in MeOH (30 ml) was added NaOH (1.0 M in water, 3.47 ml, 3.47 mmol) at rt, and the resulting mixture was stirred for 4 h. The mixture was neutralized with aq.1N-HCl and concentrated in vacuo, then extracted with CHCl3. The organic layer was washed with brine, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (3:1) as eluent to give N-Boc-5-(S)-hydroxymethyl-2-(S)-benzyloxymethylpyrrolidine (847 mg, 91%) as a colorless oil. 1H-NMR (CDCl3) δ1.41 (s, 9 H), 1.57 (brs, 1 H), 1.95-1.97 (m, 2 H), 2.05-2.18 (m, 1 H), 3.36 (t, J=8.4 Hz, 1 H), 3.56-3.62 (m, 2 H), 3.67-3.72 (m, 2 H), 3.95 (brs, 1 H), 4.03 (brs, 1 H), 4.51 (s, 1 H), 7.28-7.37 (m, 5H); MS (FAB) m/z, 322 (M++H).

Workup

  1. concentration1N-HCl and concentrated in vacuo
  2. extractionextracted with CHCl3
  3. washThe organic layer was washed with brine
  4. dry with materialdrying over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel with hexane-EtOAc (3:1) as eluent

Sources & evidence

ORD record
ord-b21259b1697e4384a61da01abf0530cc
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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