Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]-4-methylsulfonyloxypyrrolidine

HRID 975673Notes

Reaction equation

HRID 975673 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[CH2:17][CH2:18][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH2:24][O:25][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].Cl>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][CH2:18][N:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH2:24][OH:25])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54342959(2R,4R)-1-allyloxycarbonyl-2-[2-(2-(t-butyldimethylsilyloxymethyl) imidazol-1-yl)ethyl]-4-methylsulfonyloxypyrrolidine

Product 1

HCID 54269204(2R,4R)-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]-4-methylsulfonyloxypyrrolidineYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-{2-(t-butyldimethylsilyloxymethyl)imidazol-1-yl}ethyl]-4-methylsulfonyloxypyrrolidine (34.5 g) in methanol (170 ml) was added concentrated hydrochloric acid (17 ml) dropwise under cooling in an ice bath. After stirring for 10 minutes, the mixture was warmed to room temperature and stirred for another 3 hours. The mixture was quenched by the addition of a solution of sodium methoxide in methanol (28% W/W, 39.4 g), then ethyl acetate (340 ml) was added. The precipitate was filtered off and the filtrate was concentrated to give a crude oil. The oil was chromatographed on a 300 g of silica gel eluting with a mixture of chloroform and methanol (100:0 to 95:5) to give (2R,4R)-1-allyloxycarbonyl-2-[2-(2-hydroxymethylimidazol-1-yl) ethyl]-4-methylsulfonyloxypyrrolidine (15.7 g) as a light brown paste.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringstirred for another 3 hours
  3. customThe mixture was quenched by the addition of a solution of sodium methoxide in methanol (28% W/W, 39.4 g)
  4. additionethyl acetate (340 ml) was added
  5. filtrationThe precipitate was filtered off
  6. concentrationthe filtrate was concentrated
  7. customto give a crude oil
  8. customThe oil was chromatographed on a 300 g of silica gel eluting with a mixture of chloroform and methanol (100:0 to 95:5)

Sources & evidence

ORD record
ord-5acc2d7097a9405187baa099f1c463dd
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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