Trifluoroacetic acid → (4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyne
Reaction equation
C(OC([C:8]#[C:9][CH2:10][CH:11]([OH:23])[CH:12]([OH:22])[CH:13]([NH2:21])[CH2:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=O)(C)(C)C.FC(F)(F)C(O)=O.CCOC(C)=O>C(Cl)Cl.CCCCCC>[NH2:21][C@@H:13]([CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C@@H:12]([OH:22])[C@@H:11]([OH:23])[CH2:10][C:9]#[CH:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the diol heptyne of Step 6 isomer (2.85 mmol) in CH2Cl2 (5.5 mL) was added trifluoroacetic acid (71.3 mmol). The reaction was monitored by TLC (50% EtOAc in hexane). After 30 minutes the solution was concentrated and an aqueous 1.0N NaOH solution (7 mL) was added. The solution was extracted with EtOAc (4×10 mL). The organic layer was dried with MgSO4. The filtrate was concentrated to give the title amine as a white sticky solid (0.67 g, 100% yield). The 1H, 13C and APT NMR spectral data were consistent with the prepared structure.
Workup
- concentrationAfter 30 minutes the solution was concentrated
- additionan aqueous 1.0N NaOH solution (7 mL) was added
- extractionThe solution was extracted with EtOAc (4×10 mL)
- dry with materialThe organic layer was dried with MgSO4
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-018adf16dffc428588262d40a975ade7
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06342624B1
Reaction notes
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