Triethylamine → HCID 13294373, compound

HRID 1077921Notes

Reaction equation

HRID 1077921 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-e541d15208034169b517a8c1f996ca10
Source dataset
uspto-grants-1996_08
Patent number
US05545658

Reaction notes

Loading…