Methyl iodide → methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylate

HRID 736817

Reaction equation

[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Li])CCC.[C:22]1([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25][CH2:24][CH:23]=1.IC>>[CH2:1]([N:8]([C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[C@@H:23]1[CH2:24][CH2:25][CH2:26][C@:22]1([CH3:17])[C:27]([O:29][CH3:30])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 549129Methyl cyclopent-1-ene-1-carboxylate

HCID 1268086(+)-Benzylphenethylamine

HCID 178418339Butyllithium

Product 1

HCID 86607912methyl (1S,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylateYield 78%

Procedure

According to the procedure of Example 53, Step 1, using (R)-N-benzyl-N-α-methylbenzylamine (4.2 mL, 4.24 g, 20 mmol), n-butyllithium (2.4 M, 7.4 mL), methyl 1-cyclopentene-1-carboxylate (1.3 mL, 1.29 g, 10.2 mmol), and iodomethane (1.3 mL). methyl (1S,2R)-2-{benzyl[(l R)-1-phenylethyl]amino}-1-methylcyclopentanecarboxylate (2.804 g, 7.97 mmol, 78%) was obtained as a brown oil after column chromatography on silica gel eluting with 5% ethyl acetate/hexanes. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 0.63 (s, 3H) 1.18-1.29 (m, 5H) 1.52-1.64 (m, 1H) 1.74-1.83 (m, J=12.44, 7.67, 7.67, 2.53 Hz, 1H) 1.85-1.92 (m, 1H) 2.03-2.12 (m, 3H) 2.88 (dd, J=10.86, 7.33 Hz, 1H) 3.50-3.54 (m, 3H) 3.57-3.64 (m, 1H) 3.72-3.77 (m, 1H) 3.83 (q, J=6.82 Hz, 1H) 7.17-7.21 (m, 1H) 7.24-7.35 (m, 6H) 7.50 (d, J=7.33 Hz, 2H).

Sources & evidence

ORD record: ord-85d228a13f16435cb6ceeb59ddbd0a73
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Linked notes

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