Hydrochloric Acid → HCID 69939986, compound

HRID 1058270Notes

Reaction equation

HRID 1058270 reaction equation
C(S([NH:7][CH:8]([C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[CH2:12][OH:13])[CH3:9])=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:7][CH:8]([C:10]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:11]=1[CH2:12][OH:13])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69940220HCID 69940220, compound

Product 1

HCID 69939986HCID 69939986, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(1-tert-butylsulfinamidylethyl)-5-chlorobenzyl alcohol from step 2 of the L-519,502 synthesis (isomer 2, 0.654 g, 2.23 mmol) in MeOH (10 mL) at ambient temperature was added 4M HCl in dioxane (1.12 mL, 4.46 mmol). The resulting solution was stirred at ambient temperature for 0.5 h, then concentrated in vacuo. The residue was partitioned between EtOAc and water basified to pH=8 with saturated NaHCO3 solution. The EtOAc layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure. 2-(1-aminoethyl)-5-chlorobenzyl alcohol was obtained as a pink oil that crystallizes on sitting (0.3 g; HPLC RT=2.07 min, method A; 1H NMR, 400 MHz, CDCl3, 7.32 ppm (d, 1H), 7.29 ppm (d, 1H), 7.24 ppm (dd, 1H), 4.76 ppm (d, 1H), 4.65 ppm (d, 1H), 4.34 ppm (q, 1H), 3.4 ppm (br s, 3H), 1.7 ppm (d, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customThe EtOAc layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe filtrate solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8d90c877c1c44f599a3c71447eff91c1
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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