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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 874316Generated: October 30, 2026

4-Fluorobenzaldehyde → (+/-)-(E)-3-{1'-(4-Fluoro-benzyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester

https://huagongshe.com/reaction/874316

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-FluorobenzaldehydeHCID 68023—
ReactantSodium cyanoborohydrideHCID 5003444—
Reactant(+/-)-(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl esterHCID 67071413—
Product(+/-)-(E)-3-{1'-(4-Fluoro-benzyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl esterHCID 67071482—

Reaction Steps

(±)-(E)-3-{1′-(4-Fluoro-benzyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3′-piperidin]-6-yl}-acrylic acid methyl ester was synthesized starting from Intermediate 5 (339 mg, 1.00 mmol), according to the procedure described in Example 40, Step A, using 4-fluorobenzaldehyde (0.13 ml, 1.2 mmol) and NaBH3CN (76 mg, 1.2 mmol). The product was obtained as a white solid (320 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08980877B2
Source datasetuspto-grants-2015_03
ORD IDord-195d122c9c8c4a7e931ab3ed5c41979d
Source noteuspto-grants-2015_03