2,2,2-Trifluoroethanol → HCID 21906044, compound

HRID 1246755Notes

Reaction equation

HRID 1246755 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]([F:20])([F:19])[CH2:17]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:15][C:16]([F:20])([F:19])[CH2:17][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 21906044HCID 21906044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-1-piperidinecarboxylate (30.0 g), 2,2,2-trifluoroethanol (149 g) and triphenylphosphine (58.6 g) in tetrahydrofuran (450 ml) was slowly added diethyl azodicarboxylate (38.9 g) at 8° C. The mixture was stirred at room temperature for 2 hours, and at 60° C. for 8 hours. The reaction mixture was concentrated in vacuo to give the crude product of the title compound. The crude product was purified by chromatography on silica gel.

Workup

  1. customat 8° C
  2. waitat 60° C. for 8 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-958ad9f5470f4ea487cf08625bfba677
Source dataset
uspto-grants-2006_10
Patent number
US07129243B2

Reaction notes

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