HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2400919Generated: October 30, 2026
Sodium Carbonate → (3R,4R)-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate
https://huagongshe.com/reaction/2400919
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | N,N-Diethylethanamine trihydrofluoride | HCID 175505 | — |
| Reactant | tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate | HCID 10103880 | — |
| Product | (3R,4R)-tert-Butyl 3-fluoro-4-hydroxypyrrolidine-1-carboxylate | HCID 57416936 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796256B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-50eaa568ad384baaa3ba7372077ac74a |
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| Source note | uspto-grants-2014_08 |
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