Acetic Acid → (S)-3-((S)-1,2-dihydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester

HRID 533377Notes

Reaction equation

HRID 533377 reaction equation
CC(O)=[O:3].[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([CH:17]2[CH2:19][O:18]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O>C1(C)C=CC=CC=1>[C:5]([O:9][C:10]([N:12]1[CH2:16][CH2:15][C@H:14]([C@H:17]([OH:3])[CH2:19][OH:18])[CH2:13]1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 86650332(S)-3-oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66857637(S)-3-((S)-1,2-dihydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(R,R)-(−)-N,N′-Bis(3,5-di-t-butylsalicylidene)-1,2-cyclohexanediaminocobalt (II) (32.6 mg, 53.9 μmol) was dissolved in toluene (2.0 mL). AcOH was added (6.1 μL), and the resulting mixture was stirred at room temperature for 1 hour under air. The mixture was then concentrated and dried under high vacuum. (S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (2.3 g, 10.8 mmol) was added, followed by water (97.1 μL), and the resulting mixture was stirred vigorously for 6 hours. Hexanes (15 mL) was added. The resulting solid was manually crushed and additional hexanes was added and stirred until the red solid became a yellowish precipitate. The precipitate was filtered and washed with 2 portions of hexanes. The precipitate was dried under vacuum to yield (S)-3-((S)-1,2-dihydroxyethyl)pyrrolidine-1-carboxylic acid t-butyl ester as an off-white solid (1.3 g). The filtrate was concentrated and purified by SiO2 flash chromatography (0-100% EtOAc in hexanes) to yield (S)—(R)-3-oxiranylpyrrolidine-1-carboxylic acid t-butyl ester as an oil (970 mg).

Workup

  1. concentrationThe mixture was then concentrated
  2. customdried under high vacuum
  3. stirringthe resulting mixture was stirred vigorously for 6 hours
  4. customThe resulting solid was manually crushed
  5. stirringstirred until the red solid
  6. filtrationThe precipitate was filtered
  7. washwashed with 2 portions of hexanes
  8. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-2cd6526372b4466bb9348f6f8ff48c32
Source dataset
uspto-grants-2014_10
Patent number
US08853255B2

Reaction notes

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