Hydrochloric Acid → (1R,2S)-2-Methoxy-2,3-dihydro-1H-inden-1-amine

HRID 222184Notes

Reaction equation

HRID 222184 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:4]1[NH:12]C(=O)OC(C)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:4]1[NH2:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 86614253tert-Butyl [(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]carbamate

Product 1

HCID 28109796(1R,2S)-2-Methoxy-2,3-dihydro-1H-inden-1-amineYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl [(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]carbamate (253 mg, 0.961 mmol) was added a 4.00 M solution of hydrochloric acid in 1,4-dioxane (5.00 mL) and the mixture was stirred for 10 min, after which a white solid crashed out. The suspension was concentrated in vacuo and co-evaporated with toluene to afford a white solid, which was dissolved in water. The solution was adjusted to pH 10 via addition of sodium carbonate. The mixture was then extracted with diethyl ether (3×30 mL) and the organic extracts were concentrated in vacuo to afford the title compound (150 mg, 99%). LC/MS: Rt=0.85 min, ES+ 164 (AA standard).

Workup

  1. concentrationThe suspension was concentrated in vacuo and co-evaporated with toluene
  2. customto afford a white solid, which
  3. extractionThe mixture was then extracted with diethyl ether (3×30 mL)
  4. concentrationthe organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-394a139060d645dca8dcaff3ef53aa23
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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