Benzyl chloroformate → HCID 178523389, compound

HRID 448997Notes

Reaction equation

HRID 448997 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[OH-].[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>>[CH2:18]([O:17][C:15]([NH:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 178511262HCID 178511262, compound

Product 1

HCID 178523389HCID 178523389, compoundYield 93%

Procedure

trans-4-(Aminomethyl)cyclohexanecarboxylic acid (10.00 g, 0.06361 mol), in a 10% aq solution of NaOH (5.60 g in 55 mL) was cooled to 0° C. and treated over 15 min with vigorous stirring, with benzyl chloroformate (11 mL, 0.076 mol). After one hour the solution was acidified (1M HCl(aq)) and the resulting the white precipitate collected by filtration, washed with water and hexane then dried in vacuo oven overnight to afford 17.23 g of the title compound. 1H NMR (400 MHz, CDCl3): δ 0.93-0.99 (m, 2H), 1.38-1.46 (m, 2H), 1.82-1.85 (m, 2H), 2.03-2.06 (m, 2H), 2.25 (m, 1H), 3.06 (t, J=5.6 Hz, 2H), 4.83 (m, 1H), 5.09 (s, 2H), 7.31-7.36 (m, 5H). MS (ES+): m/z 292 [MH+].

Workup

  1. filtration(1M HCl(aq)) and the resulting the white precipitate collected by filtration
  2. washwashed with water and hexane
  3. customthen dried in vacuo oven overnight

Sources & evidence

ORD record
ord-0a5ecce139cb45919da1b1f7bc03970d
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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