Trifluoroacetic acid → (3aR,5R,6aR)-5-Amino-3a-(7-(trifluoromethyl)-1,2,3,4-tetrahydro-isoquinoline-2-carbonyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide

HRID 571356Notes

Reaction equation

HRID 571356 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:17][C@H:11]2[CH2:12][N:13]([C:15]#[N:16])[CH2:14][C@@:10]2([C:18]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][C:24]([C:30]([F:33])([F:32])[F:31])=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=[O:36]>C(Cl)Cl>[NH2:7][C@@H:8]1[CH2:17][C@H:11]2[CH2:12][N:13]([C:15]([NH2:16])=[O:36])[CH2:14][C@@:10]2([C:18]([N:20]2[CH2:29][CH2:28][C:27]3[C:22](=[CH:23][C:24]([C:30]([F:32])([F:31])[F:33])=[CH:25][CH:26]=3)[CH2:21]2)=[O:19])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131732813tert-Butyl((3aR,5R,6aR)-2-Cyano-3a-(7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)octahydrocyclopenta[c]pyrrol-5-yl)carbamate

Product 1

HCID 86708901(3aR,5R,6aR)-5-Amino-3a-(7-(trifluoromethyl)-1,2,3,4-tetrahydro-isoquinoline-2-carbonyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step A (0.03 g, 0.627 mmol) in TFA (1 mL) and DCM (1 mL) was stirred at rt for 1.5 h. The volatile organic compounds were removed by evaporation, and the residue was diluted with DCM and evaporated again to give the product as a TFA salt. LC/MS: C19H23F3N4O2: m/z 397.2 (M+H).

Workup

  1. customThe volatile organic compounds were removed by evaporation
  2. additionthe residue was diluted with DCM
  3. customevaporated again

Sources & evidence

ORD record
ord-3b2bb0c688524ecab40b41c1cb62094e
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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