Ammonia → 1-(3-(3-Aminopropyl)phenyl)-3-isopropyl-4-methylpent-1-yn-3-ol

HRID 658841Notes

Reaction equation

HRID 658841 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][C:17]([OH:24])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH:10]=1)=O.C(Cl)Cl.N>CO>[NH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]([CH:21]([CH3:23])[CH3:22])([OH:24])[CH:18]([CH3:20])[CH3:19])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 866284522,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-isopropyl-4-methylpent-1-ynyl)phenyl)propyl)acetamide

Product 1

HCID 251669601-(3-(3-Aminopropyl)phenyl)-3-isopropyl-4-methylpent-1-yn-3-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Deprotection of 2,2,2-trifluoro-N-(3-(3-(3-hydroxy-3-isopropyl-4-methylpent-1-ynyl)phenyl)propyl)acetamide following the method used in Example 2 followed by flash chromatography (9:1 CH2Cl2: 7 M NH3 in MeOH) gave 1-(3-(3-aminopropyl)phenyl)-3-isopropyl-4-methylpent-1-yn-3-ol as a clear oil. Yield (0.835 g, 82%): 1H NMR (400 MHz, DMSO-d6) δ 7.15-7.26 (m, 4H), 4.82 (br s, 1H), 2.56 (t, J=7.6 Hz, 2H), 2.47-2.52 (m, 2H), 1.86 (quint, J=6.8 Hz, 2H), 1.59 (quint, J=6.8 Hz, 2H), 1.56 (br.s, 2H), 1.05 (d, J=6.8 Hz, 6H), 1.03 (d, J=6.8 Hz, 6H).

Sources & evidence

ORD record
ord-38cca5b6fd4d4385b4f3ad9f130fe627
Source dataset
uspto-grants-2011_12
Patent number
US08076516B2

Reaction notes

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