1-Benzylcyclopentanol → HCID 58979699, compound

HRID 1180729Notes

Reaction equation

HRID 1180729 reaction equation
[CH2:1]([C:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:14]([C@@H:17]([CH2:22][CH2:23][CH2:24][CH3:25])[C:18]([O:20][CH3:21])=[O:19])=[C:15]=[O:16]>C1(C)C=CC=CC=1>[CH2:1]([C:8]1([O:13][C:15]([NH:14][C@@H:17]([CH2:22][CH2:23][CH2:24][CH3:25])[C:18]([O:20][CH3:21])=[O:19])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5642421-BenzylcyclopentanolHCID 86597003HCID 86597003, compound

Product 1

HCID 58979699HCID 58979699, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To 840.8 mg (4.77 mmol) of 1-benzylcyclopentanol in 2.4 mL of toluene was added 816.7 mg (4.77 mmol) of methyl(2S)-2-isocyanatohexanoate. The mixture was heated at 85° C. for 4 d. The solution was concentrated and the residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:4) to give 1.31 g (79%) of methyl(2S)-2-({[(1-benzylcyclopentyl)oxy]carbonyl}amino)hexanoate. Rf=0.31 (1:4 ethyl acetate:hexanes); 1H NMR (300 MHz, DMSO-d6) δ 7.37 (d, J=8 Hz, 1H), 7.27-7.06 (m, 5H), 4.00 (m, 1H), 3.64 (s, 3H), 3.19 (ABq, JAB=14 Hz, ΔνAB=9 Hz, 2H), 1.96-1.78 (m, 2H), 1.76-1.38 (m, 8H), 1.36-1.14 (m, 4H), 0.86 (t, J=7 Hz, 3H); ES-LCMS m/z 370 (M+Na).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with an ethyl acetate

Sources & evidence

ORD record
ord-d681a99257f44485abb531d9bd25f2eb
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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