Benzyl Alcohol → Benzyl 1-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane Acetate

HRID 457283Notes

Reaction equation

HRID 457283 reaction equation
[Cl:1][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:8])[CH:3]([CH3:5])[CH3:4].C1(N=C=NC2CCCCC2)CCCCC1.[CH2:36](O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][CH:2]([O:6][C:7]([NH:9][CH2:10][C:11]1([CH2:17][C:18]([O:20][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 226420071-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-Cyclohexane Acetic Acid

Product 1

HCID 66584247Benzyl 1-{[(alpha-Chloroisobutoxy)carbonyl]aminomethyl}-1-Cyclohexane AcetateYield 62%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (93) (1.02 g, 3.34 mmol) in dichloromethane was added 1,3-dicyclohexylcarbodiimide (758 mg, 3.67 mmol). After stirring at room temperature for 30 min, benzyl alcohol (380 μL, 3.67 mmol) and 4-(dimethylamino)pyridine (catalytic amount) were added. The resulting mixture was stirred at room temperature of 16 h. After filtration, the filtrate was washed with 10% citric acid, dried over Na2SO4, and concentrated. Chromatography of the residue on silica gel, eluting with 10% ethyl acetate/hexane, gave 820 mg (62%) of the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.03 (d, J=6.4 Hz, 3H), 1.05(d, J=6.4 Hz, 3H), 1.36–1.53 (m, 10H), 2.13 (m, 1H), 2.35 (s, 2H), 3.22 (m, 2H), 5.11 (s, 2H), 5.49 (t, 1H), 6.32 (d, J=4.8 Hz), 1H), 7.34 (m, 5H). MS (ESI) m/z 396.24 (M+H+).

Workup

  1. stirringThe resulting mixture was stirred at room temperature of 16 h
  2. filtrationAfter filtration
  3. washthe filtrate was washed with 10% citric acid
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. washChromatography of the residue on silica gel, eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-36e93bf5aeeb43548b1ef3645a38ec10
Source dataset
uspto-grants-2007_03
Patent number
US07186855B2

Reaction notes

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