1-Bromo-3-chlorobenzene → (5R,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate

HRID 2038566Notes

Reaction equation

HRID 2038566 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][C:4]2([CH2:10][C@@H:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7]2)[O:3]1.[Cl:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[CH:30][CH:31]=1>>[Cl:25][C:26]1[CH:31]=[C:30]([N:6]2[CH2:5][C@:4]3([CH2:10][C@@H:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[N:8]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:7]3)[O:3][C:2]2=[O:1])[CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 79281-Bromo-3-chlorobenzeneHCID 59547287(8S)-di-tert-butyl 2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate

Product 1

HCID 59547336(5R,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylateYield 21.7%

Procedure

Following the procedure from Example 1 step C using (8S)-di-tert-butyl 2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate (2) (189 mg, 0.55 mmol, 1 eq.) and 3-chloro bromobenzene (60 μl, 0.55 mmol, 1 eq.) gave 54 mg (119) of (5R,8S)-di-tert-butyl 3-(3-chlorophenyl)-2-oxo-1-oxa-3,7-diazaspiro[4.4]nonane-7,8-dicarboxylate (A4). 1H NMR (300 MHz, DMSO) 7.68 (m, 1H), 7.55-7.38 (m, 2H), 7.2 (m, 1H), 4.38-4.28 (m, 1H), 4.2-4.05 (m, 2H), 3.75-3.6 (m, 2H), 2.7-2.4 (m, 2H), 1.4 (m, 18H).

Sources & evidence

ORD record
ord-17490f3ceead4175aeec6e50aabf4080
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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