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

HRID 874316Notes

Reaction equation

HRID 874316 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.[F:30][C:31]1[CH:38]=[CH:37][C:34](C=O)=[CH:33][CH:32]=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][C:34]4[CH:37]=[CH:38][C:31]([F:30])=[CH:32][CH:33]=4)[CH2:14]3)[NH:12][C:11](=[O:27])[C:10]=2[CH:28]=1

Participants

4

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 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 67071482(+/-)-(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

Procedure

(±)-(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).

Sources & evidence

ORD record
ord-195d122c9c8c4a7e931ab3ed5c41979d
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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