Trifluoroacetic acid → HCID 178504879, compound

HRID 1257729Notes

Reaction equation

HRID 1257729 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:19][S:16]([CH2:15][CH2:14][C@H:11]1[CH2:10][CH2:9][C@H:8]([NH2:7])[CH2:13][CH2:12]1)(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453930HCID 178453930, compound

Product 1

HCID 178504879HCID 178504879, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans [4-(2-methanesulfonyl-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (900 mg, 2.95 mmol) was dissolved in DCM (7 mL) and trifluoroacetic acid (7 mL) was added. The mixture was stirred at room temperature for 1 h, then concentrated. The residue was taken up in methanol and purified by Isolute® SCX-2 column (gradient: methanol to 2 M NH3 in methanol) to give 594 mg (98%) of trans 4-(2-methanesulfonyl-ethyl)-cyclohexylamine. LCMS (method Q, ESI): RT=0.48 min, m+H=206.1; NMR (400 MHz, DMSO) δ: 3.09 (m, 2H), 2.93 (s, 3H), 2.48-2.41 (m, 1H), 1.78-1.64 (m, 4H), 1.58-1.51 (m, 2H), 1.30-1.18 (m, 1H), 1.03-0.82 (m, 4H).

Workup

  1. concentrationconcentrated
  2. custompurified by Isolute® SCX-2 column (gradient: methanol to 2 M NH3 in methanol)

Sources & evidence

ORD record
ord-6d134cdc91834cbc89f7b3448ca2117b
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…