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

HRID 874312Notes

Reaction equation

HRID 874312 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=O.[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]([CH3:19])[CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 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 67071521(+/-)-(E)-3-{1'-Methyl-3,4-dihydro-4-oxo-spiro[2H-(1,3)-benzoxazine-2,3'-piperidin]-6-yl}-acrylic acid methyl ester

Procedure

(±)-(E)-3-{1′-Methyl-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 (300 mg, 0.88 mmol), according to the procedure described in Example 40, Step A, using formaldehyde (0.85 ml, 1.1 mmol) and NaBH3CN (68 mg, 1.1 mmol). The product was obtained as a white solid (240 mg).

Sources & evidence

ORD record
ord-3f132ace9e9b46548acc94ea035ef899
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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