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

HRID 874319Notes

Reaction equation

HRID 874319 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][N:15]([C:19](OC(C)(C)C)=O)[CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1.[C:30]1([CH2:36]C=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[BH3-]C#N.[Na+]>>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]2[O:26][C:13]3([CH2:18][CH2:17][CH2:16][N:15]([CH2:19][CH2:36][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1

Participants

4

Reactant 3

HCID 998PhenylacetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67071413(+/-)-(E)-3-{1'-tert-butoxycarbonyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester

Product 1

HCID 67071484(+/-)-(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

Procedure

(±)-(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).

Sources & evidence

ORD record
ord-643810e8841d42fb9ecb345c19f6375c
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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