Triethylamine → HCID 15592690, compound

HRID 2309231Notes

Reaction equation

HRID 2309231 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([CH:14]([O:19]C(=O)NC(C2C=CC=CC=2)C)[C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[SiH](Cl)Cl>C1(C)C=CC=CC=1.[NH4+].[Cl-]>[O:1]([C:8]1[N:13]=[C:12]([C@@H:14]([C:15]([F:18])([F:16])[F:17])[OH:19])[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 14074449HCID 14074449, compound

Product 1

HCID 15592690HCID 15592690, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A stirred solution of 1.28 g (3.08 mmol) of the [S-(R*,S*)] carbamate from Step A, 0.52 ml (380 mg, 3.7 mmol) of triethylamine, and 0.34 ml (460 mg, 3.4 mmol) of trichlorosilane in 12 ml of toluene under a nitrogen atmosphere was heated at 60° C. for 2 hours. The reaction mixture was then diluted with 50 ml of saturated aqueous NH4Cl and extracted with ether (3×25 ml). After being dried (MgSO4), the combined organic extracts were concentrated under reduced pressure and chromatography of the residue on 20 g of silica gel with 1:15 ethyl acetate/hexane afforded 667 mg (81%) of the title compound as a white solid melting at 51.5°-53.5° C.: [α]D22 =+2.0° (CHCl3, c 1.00) and [α]36522 =+4.8° (CHCl3, c 1.00). The spectral and chromatographic properties of this material were identical to those of racemic material prepared in Example 1 (Step C).

Workup

  1. extractionextracted with ether (3×25 ml)
  2. dry with materialAfter being dried (MgSO4)
  3. concentrationthe combined organic extracts were concentrated under reduced pressure and chromatography of the residue on 20 g of silica gel with 1:15 ethyl acetate/hexane

Sources & evidence

ORD record
ord-cfb2b42cf27d48bd90526ddc0d595058
Source dataset
uspto-grants-1987_09
Patent number
US04694013

Reaction notes

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