Acetic Acid → HCID 18785555, compound

HRID 1107694Notes

Reaction equation

HRID 1107694 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][S:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)CCl>[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][S:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH:8][CH:27]1[CH2:28][CH2:29][N:24]([C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride2×HCID 11254872HCID 11254872, compound

Product 1

HCID 18785555HCID 18785555, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-(2-bromobenzyl)thioaniline (7.55 g) and 1-tert-butyloxycarbonylpiperidin-4-one (6.68 g) in 2-dichloroethane (100 ml) were added acetic acid (30 ml) and sodium triacetoxyborohydride (7.1 g), and the mixture was stirred at a room temperature for 2 hours. Additional amount of sodium triacetoxyborohydride (500 mg) was added, and the mixture was further stirred at a room temperature for 2 hours. The reaction was concentrated under reduced pressure, diluted with ethyl acetate, washed successively with water, a saturated aqueous sodium hydrogen carbonate solution, and water, dried over magnesium sulfate, and the solvent was removed. The residue thus obtained was purified by chromatography on a silica gel column (250 g) to give the title compound as a resinous product (11.2 g, 91%) from the fraction eluted with n-hexane:ethyl acetate=5:1.

Workup

  1. stirringthe mixture was further stirred at a room temperature for 2 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed successively with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and water, dried over magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue thus obtained
  8. customwas purified by chromatography on a silica gel column (250 g)

Sources & evidence

ORD record
ord-2d495eb02403400595f16786995ce5b4
Source dataset
uspto-grants-2000_05
Patent number
US06063779

Reaction notes

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