Ammonium Chloride → methyl rac-(1R,2R)-1-amino-2-hydroxyindane-1-carboxylate

HRID 64444Notes

Reaction equation

[O:1]1[CH:3]2[CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C:2]12[C:11]([O:13][CH3:14])=[O:12].[N-:15]=[N+]=[N-].[Na+].[Cl-].[NH4+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.CO>[NH2:15][C:2]1([C:11]([O:13][CH3:14])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[OH:1]

Participants

Conditions

Temperature: 80 °C

Procedure

To 500 mg of methyl 6,6a-dihydro-1aH-indeno[1,2-b]oxirene-1a-carboxylate were added 860 mg of sodium azide, 309 mg of ammonium chloride, 4 ml of methanol, and 0.5 ml of water, followed by stirring at 80° C. for 2 hours. To the reaction mixture were added a saturated aqueous sodium hydrogen carbonate solution, water, and ethyl acetate to carry out a layer separation operation, and the organic layer was dried over anhydrous magnesium sulfate. To a solution of the obtained intermediate product in ethyl acetate-methanol was added 61 mg of 10% palladium-carbon (wet), followed by stirring for 6 hours under a hydrogen atmosphere. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure to obtain 0.51 g of methyl rac-(1R,2R)-1-amino-2-hydroxyindane-1-carboxylate.

Workup

customa layer separation operation
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
additionTo a solution of the obtained intermediate product in ethyl acetate-methanol was added 61 mg of 10% palladium-carbon (wet)
stirringby stirring for 6 hours under a hydrogen atmosphere
filtrationThe reaction mixture was filtered over Celite
customthe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-9eaf440d76194cf7a81ba10aa81d85a8
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447090B2

Reaction notes

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