Benzyl Alcohol → HCID 86749822, compound

HRID 743486Notes

Reaction equation

HRID 743486 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]1([CH2:14][OH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH2:17]([CH:20]1[CH2:25][CH2:24][CH2:23][NH:22][CH:21]1[C:26]([O:28][CH3:29])=[O:27])[CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl.Cl.[Cl-].[Na+]>[CH3:29][O:28][C:26]([CH:21]1[CH:20]([CH2:17][CH2:18][CH3:19])[CH2:25][CH2:24][CH2:23][N:22]1[S:2]([NH:5][C:6]([O:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])(=[O:4])=[O:3])=[O:27]

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 19424461HCID 19424461, compound

Product 1

HCID 86749822HCID 86749822, compoundYield 86.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 3.01 ml (34.72 mmol) of chlorosulfonyl isocyanate in 200 ml of dry methylene chloride was added phenylmethanol (3.61 ml, 34.72 mmol) at 0° C. After stirring the above solution for 1 hour at this temperature, a solution of 7.3 g (33.07 mmol) of methyl 3-propyl-piperidine-2-carboxylate hydrochloride in methylene chloride containing triethylamine (13.75 ml; 99.21 mmol) was added at 0° C., and the resulting mixture was stirred overnight (17 hours) allowing the mixture to warm to room temperature. The reaction mixture was diluted with the same volume of methylene chloride and 200 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride and the combined organic layer was washed with brine, dried and concentrated in vacuo. The residual oil was purified by flash chromatography (30% ethyl acetate in hexane) to yield 11.43 g (86.7%) of N-(carbobenzyloxyaminosulfonyl)-3-propyl-2-piperidinecarboxylic acid methyl ester(Formula XIV: R=CH3;R1 =H; R2 and R3 together =-[CH(propyl)(CH2)3 ]-) as an oil.

Workup

  1. additionwas added at 0° C.
  2. stirringthe resulting mixture was stirred overnight (17 hours)
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. washthe combined organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residual oil was purified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7d519d50b6494433a373fa01afe61828
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

Loading…