Triphenylphosphine → HCID 178501290, compound

HRID 1194917Notes

Reaction equation

HRID 1194917 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13]/[N:14]=[C:15](/[C:23](=[O:25])[CH3:24])\[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].O[C@@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:19]([O:18][C:16](=[O:17])/[C:15](=[N:14]\[O:13][C@H:27]1[CH2:32][CH2:31][C@H:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1)/[C:23](=[O:25])[CH3:24])([CH3:21])([CH3:20])[CH3:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178468383HCID 178468383, compoundHCID 178501284HCID 178501284, compound

Product 1

HCID 178501290HCID 178501290, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (1.62 ml) in tetrahydrofuran (5 ml) was added dropwise to a solution of tert-butyl (Z)-2-hydroxyimino-3-oxobutyrate (1.6 g), methyl cis-4-hydroxycyclohexanecarboxylate (1.9 g) and triphenylphosphine (2.7 g) in tetrahydrofuran (20 ml) over 15 min at room temperature. The mixture was stirred for 18h, then the solvent removed under reduced pressure. The residue was chromatographed on silica to give the title compound (0.93 g, 33%) as a colourless liquid. νmax (film) 2950, 1730, and 1690 cm-1. δH (CDCl3) 1.47-1.64 (3H, m), 1.53 (9H, s), 1.56 (3H, d, J 5.3 Hz), 2.05 (2H, m), 2.17 (2H, m), 2.35 (1H, m), 2.37 (3H, s), 3.69 (3H, s), and 4.24 (1H, tt, J 4.1, 10.0 Hz), δC (CDCl3) 25.2, 26.3 (2C), 28.1 (3C), 29.9 (2C), 41.6, 51.7, 82.9, 84.0, 160.6, 175.5, and 193.0. [Mass spectrum +ve ion (ammonia) MH+ (328), MNH4+ (345)].

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-762f1e9a29a64a109357603fb27a61b2
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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