Triethylamine → HCID 14348565, compound

HRID 655006Notes

Reaction equation

HRID 655006 reaction equation
[CH3:1][CH:2]([CH:6]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]([OH:10])[CH3:9])[C:3](O)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH3:9][CH:8]1[CH:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:2]([CH3:1])[C:3](=[O:4])[O:10]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 14348569HCID 14348569, compound

Product 1

HCID 14348565HCID 14348565, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2RS,3RS,4SR,5SR)-2-Methyl-3-benzylamino-4-methoxycarbonyl-5-hydroxyhexanoic acid (340 mg; 1.1 mmole) and triphenylphosphine (393 mg; 1.5 mmole) were dissolved in dry toluene (6 ml). After addition of triethylamine (151.5 mg; 1.5 mmole), the resultant mixture was cooled to -15° C. Diethyl azodicarboxylate (261 mg; 1.5 mmole) was added thereto, and the mixture was stirred at -10° to -5° C. for 1 hour. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give methyl (2RS,3SR,4RS,5RS)-tetrahydro-2,5-dimethyl6-oxo-4-benzylamino-2H-pyrane-3-c (190 mg) and methyl (2SR,3SR,4RS,5RS)-tetrahydro-2,5-dimethyl-6-oxo-4-benzylamino-2H-pyrane-3-carboxylate (55 mg). (2RS,3SR,4RS,5RS) isomer:

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6dc493a7ac5142aca8a66f8c458697c1
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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