Sulfuric Acid → HCID 22851796, compound

HRID 1034496Notes

Reaction equation

HRID 1034496 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:16])=O.[BH4-].[Na+].S(=O)(=O)(O)O>O1CCCC1.C(O)C>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:15]([N:6]2[CH2:7][C@H:8]([O:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH2:9][C@H:5]2[CH2:3][OH:2])=[O:16])=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 105722791,2-Pyrrolidinedicarboxylic acid, 4-[(methylsulfonyl)oxy]-, 1-[(4-methoxyphenyl)methyl] 2-methyl ester, (2S-trans)-

Product 1

HCID 22851796HCID 22851796, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester (79.4 g: 205 mmole) in a mixture of tetrahydrofuran (200 ml) and ethanol (300 ml), sodium borohydride (14 g) is added in several portions under ice cooling. The mixture is stirred at room temperature for 4 hours. The reaction mixture is neutralized with conc. sulfuric acid, concentrated in vacuo to approximately a half volume, diluted with water, and extracted with ethyl acetate. The extract is successively washed with aqueous sodium hydrogen carbonate, water and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2) to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (58.7 g). Yield: 81.7%. NMR δ(CDCl3) ppm: 1.8 to 2.2(m, 1H), 2.3 to 2.5(m, 1H), 3.01(s, 3H), 3.57 (d, J=4.4 Hz, 1H), 3.64(d, J=4.4 Hz, 1H), 3.81(s, 3H), 3.82 to 4.3(m,3H), 5.09(s, 2H), 5.21(br s, 1H), 6.89(d, J=8.8 Hz, 2H), 7.31(d, J=8.8 Hz,2H).

Workup

  1. additionis added in several portions under ice cooling
  2. concentrationconcentrated in vacuo to approximately a half volume
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe extract is successively washed with aqueous sodium hydrogen carbonate, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (toluene:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-c3850c6883514f8eb7d12550b2a6110f
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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