Benzyl Alcohol → HCID 19424454, compound

HRID 743481Notes

Reaction equation

HRID 743481 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.[CH:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH:17]2.Cl.[Cl-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:6]([NH:5][S:2]([N:17]1[CH:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:19]2[CH2:22][CH:16]1[CH2:21][CH2:20]2)(=[O:4])=[O:3])([O:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

8

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 70918Chlorosulfonyl isocyanateHCID 13258847Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate

Product 1

HCID 19424454HCID 19424454, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 16.61 ml (191.31 mmol) of chlorosulfonyl isocyanate in methylene chloride was added phenylmethanol (19.92 ml, 191.31 mmol) at 0° C. After stirring the above solution for 2 hours at this temperature, a solution of 30.84 g (182.2 mmol) of ethyl 2-azabicyclo[2,2,1]heptan-3-carboxylate in methylene chloride containing triethylamine (42.92 ml) was added at 0° C. and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 500 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride, the combined organic layer was concentrated in vacuo and purified by flash chromatography (30% ethyl acetate in hexane) to yield 40.75 g (58.5%) of ethyl N-(carbobenzyloxyaminosulfonyl)-2-azabicyclo [2,2,1]-heptan-3-carboxylate (Formula XIV: R=Ethyl; R1 =H; R2 and R3 together = ##STR18## as an oil.

Workup

  1. additionwas added at 0° C.
  2. stirringthe resulting mixture was stirred overnight
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. concentrationthe combined organic layer was concentrated in vacuo
  6. custompurified by flash chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c561e67f83894775ae538bfbebb52abe
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

Loading…