Hydrochloric Acid → HCID 178523817, compound

HRID 1765325Notes

Reaction equation

HRID 1765325 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.[CH2:9]([O:16][C:17](ON1C(=O)CCC1=O)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CO>[CH2:9]([O:16][C:17]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 83172Benzyl succinimido carbonateHCID 178511715HCID 178511715, compound

Product 1

HCID 178523817HCID 178523817, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of trans-4-aminocyclohexanol (35.5 g, 306.6 mmol) in methanol (621 mL) at 0° C. under nitrogen was added N-(benzyloxycarbonyloxy)succinimide (72.8 g, 291.9 mmol). The reaction mixture was slowly warmed to room temperature and after 1 d, poured into 0.25 M aqueous hydrochloric acid solution (2.13 L). The resulting slurry was stirred vigorously for 1 h and then filtered. The filtered solid was washed with water to obtain the title compound (65.65 g, 90%) as a white solid. 13C NMR (400 MHz, (CD3)2SO) δ 155.3, 137.2, 128.3, 127.7, 127.6, 68.1, 65.0, 49.1, 33.9, 30.3. 1H NMR (400 MHz, (CD3)2SO) δ 7.29 (m, 5H), 7.10 (d, J=7.9 Hz, 1H), 4.96 (d, J=2.3 Hz, 2H), 4.76 (d, J=4.0 Hz, 1H), 3.29 (s, 1H), 3.17 (br s, 1H), 1.71 (m, 4H), 1.22 (t, J=9.7 Hz, 4H).

Workup

  1. filtrationfiltered
  2. washThe filtered solid was washed with water

Sources & evidence

ORD record
ord-4d47a9b7c5fd40cc9d6a766b718a3797
Source dataset
uspto-grants-2007_06
Patent number
US07226942B2

Reaction notes

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