Trifluoroacetic acid → (R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate

HRID 1253641Notes

Reaction equation

HRID 1253641 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@H:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([O:27][CH3:28])=[O:26])[CH:23]=2)[CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl>[CH3:28][O:27][C:25]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH2:17][C@H:16]2[NH2:15])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59505324Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 55278060(R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (10 ml) was added dropwise to a solution of (R)-methyl 3-(tert-butoxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (see step-2 product of A-17) (2.0 g, 6.87 mmol, 1.0 eq.) in methylene chloride (30 ml) at 0° C. The reaction mixture was then stirred at RT for 1 h. After completion (monitored by TLC), the reaction mixture was evaporated to afford the desired product as a colorless gummy solid which was used in the next step without further purification.

Workup

  1. customAfter completion (monitored by TLC), the reaction mixture was evaporated

Sources & evidence

ORD record
ord-0b9115782839407f85e1c1fddd80da51
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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