Triethylamine → HCID 13294373, compound

HRID 1289103Notes

Reaction equation

HRID 1289103 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH:4]=[CH: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.C(N(CC)CC)C>CN(C=O)C.CCOCC>[OH:8][CH:5]1[CH2:6][CH2:7][CH:2]([NH:1][C:17]([O:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:18])[CH:3]=[CH:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 12651624HCID 12651624, compound

Product 1

HCID 13294373HCID 13294373, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.64 g of cis-4-amino-2-cyclohexen-1-ol, 10.2 g of N-(benzyloxycarbonyloxy)succinimide and 5.7 ml of triethylamine in DMF is diluted with ether after stirring, washed with saturated sodium chloride solution, dried and concentrated. Chromatography of the residue on silica gel (ethyl acetate/hexane 2:1) gives 5.62 g of benzyl (1RS,4SR)-4-hydroxy-2-cyclohexene-1-carbamate. MS: 156 (M+H)+.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6976f65b40134e55a776560fe86f274e
Source dataset
uspto-grants-1998_05
Patent number
US05747522

Reaction notes

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