Water → cis-2-Triphenylmethylaminocyclohexanol

HRID 2399734Notes

Reaction equation

HRID 2399734 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:10]1([C:16]([NH:2][C@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[OH:9])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 12228413(1R,2S)-2-aminocyclohexan-1-ol hydrochloride

Product 1

HCID 54233547cis-2-Triphenylmethylaminocyclohexanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of cis-2-aminocyclohexanol hydrochloride (4.88 g; 32 mmol) (William S. Johnson and Elliot N. Schubert, J.A.C.S., Vol. 72, pp. 2187-2190 (1950), triphenylmethylchloride (10.7 g; 38.4 mmol) and triethylamine (16 ml; 115 mmol) in 250 ml methylene chloride are refluxed for 3 hrs. then stirred at room temperature overnight. The mixture is poured into H2O and extracted with CH2Cl2 (200 ml), dried (Na2SO4) concentrated in vacuo and flash chromatographed using 9:1 7:1; hexane:EtOAc to obtain cis-2-triphenylmethylaminocyclohexanol which is used directly in the next step.

Workup

  1. extractionextracted with CH2Cl2 (200 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Sources & evidence

ORD record
ord-76b8b4c2cdec433c9a174a2e1b9b67bd
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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