Hydrochloric Acid → (R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-amine hydrochloride

HRID 1844411Notes

Reaction equation

HRID 1844411 reaction equation
CC([S@]([NH:7][C@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([F:20])([F:19])[F:18])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)C.[ClH:21].CC(S(OC)=O)(C)C>CO.O1CCOCC1>[ClH:21].[F:18][C:17]([F:19])([F:20])[C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH2:9][C@H:8]2[NH2:7])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 543690Methyl 2-methylpropane-2-sulfinateHCID 89478184(R)-2-Methyl-N-((R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfinamide

Product 1

HCID 71743688(R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-amine hydrochlorideYield 29%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Intermediate 15B (370 mg, 1.21 mmol) was stirred in MeOH (5 mL) at rt. 4N HCl in dioxane (2 mL) was added. The resulting mixture was stirred at rt for 20 min. The solvents were evaporated and CH2Cl2 (3×) was added and evaporated. The resulting white solids were vacuum dried for 1 h to give Intermediate 15 (84 mg, 0.35 mmol, 29% yield) and methyl 2-methylpropane-2-sulfinate. The HCl salt was used directly in the next step. 1H NMR (400 MHz, MeOD) δ ppm 7.57 (1 H, d, J=7.8 Hz), 7.47 (1 H, d, J=7.6 Hz), 7.25 (1 H, t, J=7.8 Hz), 4.88 (1 H, dd, J=7.8, 4.8 Hz), 3.09-3.23 (1 H, m), 2.90-3.08 (1 H, m), 2.64 (1 H, dddd, J=14.1, 8.5, 8.3, 5.7 Hz), 2.01-2.23 (1 H, m, J=14.1, 8.7, 5.3, 5.3 Hz).

Workup

  1. customThe solvents were evaporated
  2. additionCH2Cl2 (3×) was added
  3. customevaporated
  4. customdried for 1 h

Sources & evidence

ORD record
ord-d8470a57595e435da1bc2281291cf3a7
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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