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

HRID 1677920Notes

Reaction equation

HRID 1677920 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>[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

5

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 1

HCID 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 HCl 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 H2(D. The solution was adjusted to pH 10. via addition of Na2CO3. The mixture was then extracted with Et2O (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. dissolutionwas dissolved in H2(D
  4. extractionThe mixture was then extracted with Et2O (3×30 mL)
  5. concentrationthe organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-b35786cf3a224e03ba92cfba405c43b3
Source dataset
uspto-grants-2011_08
Patent number
US08008307B2

Reaction notes

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