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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 874319Generated: October 30, 2026

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

https://huagongshe.com/reaction/874319

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenylacetaldehydeHCID 998—
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'-(2-Phenyl-ethyl)-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl esterHCID 67071484—

Reaction Steps

(±)-(E)-3-{1′-(2-Phenyl-ethyl)-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 phenylacetaldehyde (0.13 ml, 1.2 mmol) and NaBH3CN (63 mg, 1.2 mmol). The product was obtained as a yellow solid (320 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08980877B2
Source datasetuspto-grants-2015_03
ORD IDord-643810e8841d42fb9ecb345c19f6375c
Source noteuspto-grants-2015_03