Water → HCID 23370160, compound

HRID 1900706Notes

Reaction equation

HRID 1900706 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11]([N:18]1[CH2:23][CH2:22][CH:21](Br)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].O>CN(C)C=O>[C:11]([N:18]1[CH2:19][CH2:20][CH:21]([S:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:22][CH2:23]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 15541517tert-Butyl 4-bromopiperidine-1-carboxylate

Product 1

HCID 23370160HCID 23370160, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To benzyl mercaptan (17 ml, 152 mmol)in dimethylformamide at 0° C. under nitrogen was added sodium hydride (80% dispersion in mineral oil, 4.38 g, 152 mmol) the solution was stirred at room temperature for 15 minutes then cooled to 0° C. prior to adding N-Boc-(4-bromo)piperidine (10.8 g, 38 mmol). The mixture was stirred for 14 h at room temperature then poured into water (50 ml), extracted with diethyl ether (2×100 ml), the organic layers combined, dried (MgSO4), filtered, evaporated, and the crude product purified by flash column chromatography using 10% ethyl acetate in hexane to yield the product as a pale yellow oil (2.86 g); δH (CDCl3) 1.46 (9H, s, t-Bu), 1.51 and 1.87 (4H, m, 3,5-piperidinyl CH2), 2.85 and 3.91 (4H, m, 2,6-piperidinyl CH2), 2.69 (1H, m, 4-piperidinyl H), 3.77 (2H, s, SCH2), and 7.24-7.32 (5H, m, ArH).

Workup

  1. temperaturethen cooled to 0° C.
  2. stirringThe mixture was stirred for 14 h at room temperature
  3. extractionextracted with diethyl ether (2×100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude product purified by flash column chromatography

Sources & evidence

ORD record
ord-2515215a94074a21bd1614330a367733
Source dataset
uspto-grants-1996_11
Patent number
US05576336

Reaction notes

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