Tryptophol → HCID 44237880, compound

HRID 2066962Notes

Reaction equation

HRID 2066962 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH:5](C2SC=CC=2)[CH2:4]1.[CH:22]1[CH:23]=[CH:24][C:25]2[NH:30][CH:29]=[C:28]([CH2:31][CH2:32]O)[C:26]=2[CH:27]=1.C[Si](O[S:39]([C:42](F)(F)F)(=O)=O)(C)C.[OH-].[Na+]>ClCCl>[CH3:1][N:2]([CH3:21])[C:3]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:8][CH2:7][C:6]2([C:29]3[NH:30][C:25]4[C:26]([C:28]=3[CH2:31][CH2:32][O:9]2)=[CH:27][CH:22]=[CH:23][CH:24]=4)[CH:5]([S:39][C:42]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)[CH2:4]1

Participants

6

Reactant 4

HCID 10685TryptopholHCID 14798Sodium HydroxideHCID 65367Trimethylsilyl triflateHCID 67406136HCID 67406136, compound

Product 1

HCID 44237880HCID 44237880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)-4-dimethylamino-4-phenyl-2-thiophenylcyclohexanone (300 mg, 0.92 mmol) together with tryptophol (148 mg, 0.92 mmol) was dissolved in dichloromethane (50 ml) and mixed with trifluoromethane sulphonic acid trimethylsilyl ester (0.2 ml, 1.1 mmol). The batch was stirred for 20 h at RT. For work up the reaction mixture was mixed with 2N NaOH (10 ml) and stirred for 2 h. The organic phase was separated and the aqueous phase extracted with dichloromethane (4×20 ml). The combined organic phases were dried with MgSO4. The solvent was then removed in a vacuum. One of the four possible diastereoisomers was isolated from the residue obtained (420 mg) as vitreous solid, which solidified after rubbing with ethanol (2 ml), by means of chromatographic purification [silica gel 60 G (10 g); cyclohexane/ethyl acetate 4:1 (150 ml)]. The product could thus be obtained with a yield of 79 mg (18%) with a melting point of 228-233° C. (from 120° C. upon crystal transformation).

Workup

  1. stirringstirred for 2 h
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with dichloromethane (4×20 ml)
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. customThe solvent was then removed in a vacuum
  6. customOne of the four possible diastereoisomers was isolated from the residue
  7. customobtained (420 mg) as vitreous solid, which
  8. customafter rubbing with ethanol (2 ml), by means of chromatographic purification [silica gel 60 G (10 g); cyclohexane/ethyl acetate 4:1 (150 ml)]
  9. customThe product could thus be obtained with a yield of 79 mg (18%) with a melting point of 228-233° C. (from 120° C. upon crystal transformation)

Sources & evidence

ORD record
ord-4a9cc80d28a540418c2349bbd1346a32
Source dataset
uspto-grants-2012_10
Patent number
US08293758B2

Reaction notes

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