Hydrochloric Acid → HCID 66674948, compound

HRID 2369192Notes

Reaction equation

HRID 2369192 reaction equation
C1([C@H](OC(=O)[NH:11][C@@H:12]2[C@@H:21]([O:22][CH3:23])[CH2:20][C:19]3[C:14](=[CH:15][C:16]([OH:24])=[CH:17][CH:18]=3)[C:13]2([CH2:27][CH3:28])[CH2:25][CH3:26])C)C=CC=CC=1.Cl.O1CCOCC1>>[NH2:11][C@H:12]1[C:13]([CH2:27][CH3:28])([CH2:25][CH3:26])[C:14]2[CH:15]=[C:16]([OH:24])[CH:17]=[CH:18][C:19]=2[CH2:20][C@@H:21]1[O:22][CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66675163HCID 66675163, compound

Product 1

HCID 66674948HCID 66674948, compoundYield 115.8%

Procedure

((2S,3S)-1,1-Diethyl-7-hydroxy-3-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid (R)-1-phenyl-ethyl ester (635 mg, 1.60 mmol) was treated with 4.0 N HCl in dioxane (6.0 mL, 24 mmol) and stirred at RT. After 3 days, the solvent was removed at reduced pressure and the residual solid was triturated with 50% dichloromethane in heptane (4 mL). The solid was collected on a Buchner funnel and dried under vacuum to give the hydrochloride salt of the title compound (462 mg). (m/z): [M+H]+ calcd for C15H23NO2 250.36; found 250.2. 1H NMR (d6-DMSO, 400 mHz) δ (ppm) 9.23 (s, 1H), 8.02 (br s, 3H), 6.92 (d, J=8.2 Hz, 1H), 6.61 (m, 2H), 3.77 (m, 1H), 3.41 (s, 3H), 3.30 (m, 1H), 3.17 (m, 1H), 2.44 (dd, J=15.9 Hz, 9.8 Hz, 1H), 1.85 (m, 2H), 1.62-1.52 (m, 2H), 0.66 (t, J=7.2 Hz, 3H), 0.55 (t, J=7.0 Hz, 3H).

Workup

  1. customthe solvent was removed at reduced pressure
  2. customthe residual solid was triturated with 50% dichloromethane in heptane (4 mL)
  3. customThe solid was collected on a Buchner funnel
  4. customdried under vacuum

Sources & evidence

ORD record
ord-60c49a16fcf449a7a2302da9a32ae7c6
Source dataset
uspto-grants-2014_04
Patent number
US08703791B2

Reaction notes

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