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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1174310Generated: November 2, 2026

Tetrabutylammonium Fluoride → benzyl (1S,3S,4S)-4-[(tert-butoxymethyl)amino]-3-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

https://huagongshe.com/reaction/1174310

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactantbenzyl (1S,3S,4S)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamateHCID 86726222—
SolventTetrahydrofuranHCID 8028—
Productbenzyl (1S,3S,4S)-4-[(tert-butoxymethyl)amino]-3-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamateHCID 8672622332.1%

Reaction Conditions

Temperature25 °C

Reaction Steps

The product from Example 113B (0.28 mmol) was treated with TBAF solution in THF (1.4 mL, 1N), stirred at 25° C. for 16 hours, concentrated and partitioned between ethyl acetate and water. The organic phase was washed with brined, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 20% ethyl acetate in dichloromethane, to give the title compound (0.055 g, 31% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07834043B2
Source datasetuspto-grants-2010_11
ORD IDord-7728d5d305be4ef6a176583305f3677e
Source noteuspto-grants-2010_11