Triethylamine → HCID 178523817, compound

HRID 1457601Notes

Reaction equation

HRID 1457601 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 178511715HCID 178511715, compound

Product 1

HCID 178523817HCID 178523817, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyloxycarbonyl chloride (12.4 ml) was added dropwise to a mixture of 10 g of trans-4-aminocyclohexanol, 13.3 ml of triethylamine and 300 ml of dichloromethane under ice-cooling, and the mixture was stirred at room temperature for one hour. The reaction mixture was washed and dried, and the solvent was removed under reduced pressure. The residue was recrystallized from an ethyl acetate solution to give 5.80 g of N-benzyloxycarbonyl-trans-4-aminocyclohexanol (yield: 27%, melting point: 148°-151° C.).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was recrystallized from an ethyl acetate solution

Sources & evidence

ORD record
ord-1ad12a57658c4708a4edcb03d4580a27
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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