Hydrochloric Acid → HCID 30080799, compound

HRID 929085Notes

Reaction equation

HRID 929085 reaction equation
[N:1]([CH2:4][C@@H:5]([OH:15])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[N+]=[N-].Cl>CC(O)C>[NH2:1][CH2:4][C@@H:5]([OH:15])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59762233HCID 59762233, compound

Product 1

HCID 30080799HCID 30080799, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (R)-1-azido-3-(4-fluoro-phenoxy)-propan-2-ol (4.83 g, 22.9 mmol) NaBH4 (1.73 g, 45.8 mmol) in iPrOH (100 mL) was stirred at 80° C. for 24 h. After cooling to RT, aq. HCl (200 mL, 0.25 M) was added, washed with CH2Cl2 (100 mL). Saturated aq. K2CO3 (150 mL) was added to the aqueous phase. The product was extracted with CH2Cl2 (2×100 mL), extracts were dried over Na2SO4 and evaporated. The residue was dried under vacuum. White solid, 2.20 g (11.9 mmol, 52%).

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with CH2Cl2 (100 mL)
  3. additionSaturated aq. K2CO3 (150 mL) was added to the aqueous phase
  4. extractionThe product was extracted with CH2Cl2 (2×100 mL), extracts
  5. dry with materialwere dried over Na2SO4
  6. customevaporated
  7. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-d6dc715199d64a50b238b024f67b2f3c
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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