Sodium Carbonate → (3R,4R)-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

HRID 2400919Notes

Reaction equation

HRID 2400919 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[CH:10]([O:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[FH:14].F.F.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]([OH:11])[C@H:10]([F:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 175505N,N-Diethylethanamine trihydrofluorideHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 57416936(3R,4R)-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate

Conditions

Temperature
90 °C

Procedure

A mixture of 6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (5.4 mmol, from Example 316) and triethylamine trihydrofluoride (5.4 mmol) was heated at 90° C. for 2 h, then cooled to rt. Aq. Na2CO3 was added and the mixture was extracted with EtOAc. The organic phase was dried (Na2SO4), concentrated and purified by silica gel chromatography (0-40% EtOAc in heptane) to afford (trans)-3-fluoro-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-50eaa568ad384baaa3ba7372077ac74a
Source dataset
uspto-grants-2014_08
Patent number
US08796256B2

Reaction notes

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