Isopropanol → (S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 533383Notes

Reaction equation

HRID 533383 reaction equation
[CH:1](O)([CH3:3])[CH3:2].[H-].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]2[CH2:21][O:20]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C1C[O:25]CC1>>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]([OH:25])[CH2:21][O:20][CH:1]([CH3:3])[CH3:2])[CH2:15]1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86650334(S)-(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66859524(S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Conditions

Temperature
0 °C

Procedure

Isopropyl alcohol (215 μL, 2.8 mmol) was dissolved in THF (428 μL), and the mixture was cooled at 0° C. NaH (33.8 mg, 1.4 mmol) was added in 4 portions, and the mixture stirred for 10 minutes at room temperature. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (200 mg, 938 μmol) was added. The resulting solution was placed in a microwave reactor for 10 minutes at 100° C., then cooled to room temperature. The mixture was extracted with Hexanes (10 mL) and washed with water (10 mL). The organic layer was collected, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography (0-100% EtOAc in hexanes) to give the title compound as a clear oil (162 mg).

Workup

  1. waitThe resulting solution was placed in a microwave reactor for 10 minutes at 100° C.
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with Hexanes (10 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3eeb55f85ac2491db6950250859519cc
Source dataset
uspto-grants-2014_10
Patent number
US08853255B2

Reaction notes

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