Hydrochloric Acid → HCID 20737859, compound

HRID 350485Notes

Reaction equation

HRID 350485 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+].Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 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)-benzyloxy methylpyrrolidine (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)-benzyloxymethyl pyrrolidine (847 mg, 91%) as a colorless oil. 1H-NMR (CDCl3) δ 1.41 (s, 9 H), 1.57 (br s, 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 (br s, 1 H), 4.03 (br s, 1 H), 4.51 (s, 1 H), 7.28–7.37 (m, 5H); MS (FAB) m/z, 322 (M++H).

Workup

  1. concentrationconcentrated 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-9be43b946c50457dbf6f346df5c3913e
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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