4-Nitrobenzyl 4-hydroxycyclohexanecarboxylate → HCID 178468375, compound

HRID 1194932Notes

Reaction equation

HRID 1194932 reaction equation
[OH:1]/[N:2]=[C:3](/[C:11](=[O:13])[CH3:12])\[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].O[CH:15]1[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:22])[CH2:17][CH2:16]1>>[N+:31]([C:28]1[CH:27]=[CH:26][C:25]([CH2:24][O:23][C:21]([C@H:18]2[CH2:19][CH2:20][C@H:15]([O:1]/[N:2]=[C:3](/[C:11](=[O:13])[CH3:12])\[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])[CH2:16][CH2:17]2)=[O:22])=[CH:30][CH:29]=1)([O-:33])=[O:32]

Participants

3

Reactant 2

HCID 212490534-Nitrobenzyl 4-hydroxycyclohexanecarboxylateHCID 178468383HCID 178468383, compound

Product 1

HCID 178468375HCID 178468375, compoundYield 29%

Procedure

tert-Butyl (Z)-2-(hydroxyimino)-3-oxobutyrate (7.36 g) was treated with 4-nitrobenzyl 4-hydroxycyclohexanecarboxylate as described in Example 4, Method 3 to give the title compound (5.1 g, 29%) as a gum. νmax (film) 2950, 1740, 1695, and 1525cm-1, δH (CDCl3) 1.53 (9H, s), 1.62 (3H, m), 1.82 (1H, m), 2.14 (4H, m), 2.37 (3H, s), 2.45 (1H, tt, J 3.7 Hz, 10.7 Hz), 4.26 (1H, tt, J 3.8, 9.8 Hz), 5.22 (2H, s), 7.51 (2H, d), and 8.24 (2H, d). δC (CDCl3) 25.2, 26.2, 28.1 (3C), 29.8, 41.6, 64.7, 82.7, 84.0, 123.8 (2C), 128.3 (2C), 143.3, 147.7, 150.7, 160.6, 174.5 and 193.0. [Mass spectrum (ammonia) MNH4+ (466)].

Sources & evidence

ORD record
ord-46adb28f01b64547a637bcc431787bc2
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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