Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl chloroformate | HCID 10928 | — |
| Reactant | HCID 57682965 | HCID 57682965 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57682963 | HCID 57682963 | 80.2% |
Reaction Steps
140 g of (1S,3R)-3-isopropoxycarbonylcyclohexanecarboxylic acid are dissolved in THF, and 100 ml of triethylamine was added. At −10° C., 68.4 ml of ethyl chloroformate were added dropwise, and the suspension was stirred overnight. After filtration through celite, 55 g of sodium borohydride are added at 0° C., and the suspension is stirred at RT for a further 6 h. A further 25 g of sodium borohydride are added, and the suspension is stirred overnight. Water is added and the solution was stirred for 2 h. The phases are separated and the aqueous phase is extracted with MTBE, and the combined organic phases were washed with sat. NaCl solution, dried over MgSO4 and concentrated. 105 g of isopropyl (1R,3S)-3-hydroxymethylcyclohexanecarboxylate were obtained as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07538131B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-c4a80989496f4c90a6b2c1ca8661c83c |
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| Source note | uspto-grants-2009_05 |
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