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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2210930Generated: November 1, 2026

Trifluoroacetic acid → (4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyne

https://huagongshe.com/reaction/2210930

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
Reactant(4S,5R,6S)-N-[(tert-Butyloxy) carbonyl]-6-amino-7-cyclohexyl-4,5-dihydroxyhept-1-yneHCID 15281986—
SolventDichloromethaneHCID 6344—
Product(4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyneHCID 15281987104.3%

Reaction Steps

A solution of compound of Step 6 (0,926 g, 2.85 mmol) and trifluoroacetic acid (5.49mL, 71.3mmol) in CH2Cl2 (5.49 mL) was stirred at room temperature for 30 minutes and then concentrated in vacuo. The residue was dissolved in 1.0 N KOH (7 mL) and extracted with ethyl acetate (4×10 mL). The combined organic layers were dried over MgSO4 and then concentrated to give the title amine as an off-white solid (0.67 g, 100% yield). 1H and 13C NMR spectral data were consistent with the proposed structure.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05461074
Source datasetuspto-grants-1995_10
ORD IDord-2cc3a926bc7048a4adbfdfe2cacd984a
Source noteuspto-grants-1995_10