Iodoethane → HCID 86607915, compound

HRID 736823

Reaction equation

C([NH:8][C@H](C)C1C=CC=CC=1)C1C=CC=CC=1.C([Li])C[CH2:19][CH3:20].[C:22]1([C:27]([O:29][CH3:30])=[O:28])[CH2:26][CH2:25][CH2:24][CH:23]=1.ICC>>[NH2:8][C@@H:23]1[CH2:24][CH2:25][CH2:26][C@:22]1([CH2:19][CH3:20])[C:27]([O:29][CH3:30])=[O:28]

Participants

Reactant 4

HCID 6340Iodoethane

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

HCID 1268086(+)-Benzylphenethylamine

HCID 178418339Butyllithium

Product 1

HCID 86607915HCID 86607915, compound

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 iodoethane (1.6 mL, 3.12 g, 20 mmol), methyl (1S,2R)-2-amino-1-ethylcyclopentanecarboxylate was obtained as a mixture of two components (1.103 g) after purification on silica gel, eluting with 2% ethyl acetate/hexanes.

Sources & evidence

ORD record: ord-d7b5ccc4a5f24e288786848fc76d7ae0
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Linked notes

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