Hydrochloric Acid → HCID 86715441, compound

HRID 1522893Notes

Reaction equation

HRID 1522893 reaction equation
[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C@@H:7]([CH3:29])[CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:3]1.Cl>>[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C@@H:7]([CH3:29])[CH2:8][OH:9])[CH2:3]1

Participants

3

Procedure

(R)-3-Fluoro-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidine (732 mg, 1.87 mmol) and HCl (2N in Et2O, 1.4 mL, 2.8 mmol) were stirred at room temperature for 5 h. The solvent was decanted off, and the solid was dissolved in DCM (30 mL). The solution was washed (sat'd K2CO3), dried (Na2SO4), and concentrated under reduced pressure. The crude material was purified on a silica gel column to yield (S)-2-((R)-3-fluoropyrrolidin-1-yl)propan-1-ol (115 mg) as a clear oil. 1H NMR (DMSO-d6): δ 5.26-5.00 (m, 1H), 4.42 (t, 1H), 3.50 (m, 1H), 3.22 (m, 1H), 2.90-2.65 (m, 3H), 2.45-2.20 (m, 2H), 2.15-1.75 (m, 2H), 1.00 (d, 3H).

Workup

  1. customThe solvent was decanted off
  2. dissolutionthe solid was dissolved in DCM (30 mL)
  3. washThe solution was washed (sat'd K2CO3)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-750019acc905455bae2673c819d70eee
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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