Sodium bis(trimethylsilyl)amide → HCID 69270199, compound

HRID 458981Notes

Reaction equation

HRID 458981 reaction equation
[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)[CH2:8][CH2:9][CH:10]1[NH:14][C:13](=[O:15])[CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:42][O:43][C:44](=[O:55])[C:45]1[CH:50]=[CH:49][C:48]([CH2:51][CH2:52][CH2:53]Br)=[CH:47][CH:46]=1>>[CH3:42][O:43][C:44](=[O:55])[C:45]1[CH:50]=[CH:49][C:48]([CH2:51][CH2:52][CH2:53][N:14]2[C:13](=[O:15])[CH2:12][CH2:11][CH:10]2[CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:31])[CH3:30])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:18]=2)=[CH:47][CH:46]=1

Participants

4

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10801120Methyl 4-(3-bromopropyl)benzoateHCID 22712496HCID 22712496, compound

Product 1

HCID 69270199HCID 69270199, compoundYield 61.8%

Procedure

Analogous to the procedure described for Example 1A, Step D, 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (200 mg, 0.455 mmol) was alkylated with NaHMDS (1M in THF, 0.55 mL, 0.55 mmol) and 4-(3-bromo-propyl)-benzoic acid methyl ester (128 mg, 0.501 mmol) to yield 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-phenoxy-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (173.1 mg). 1H NMR (CDCl3) δ7.94 (d, 2H), 7.32 (m, 2H), 7.25–7.19 (m, 3H), 7.09 (m, 1H), 6.98 (d, 2H), 6.88–6.81 (m, 3H), 3.88 (s, 3H), 3.84 (m, 1H), 3.64 (m, 1H), 3.50 (m, 1H), 2.95 (m, 1H), 2.76–2.57 (m, 4H), 2.37 (m, 2H), 2.03 (m, 1H), 1.92–1.67 (m, 3H), 1.56 (m, 1H), 1.46–1.25 (m, 3H), 0.84 (s, 9H), −0.04 (d, 3H), −0.15 (d, 3H).

Sources & evidence

ORD record
ord-da9daea9e2e842239c6fc130c0c14bcf
Source dataset
uspto-grants-2007_03
Patent number
US07192979B2

Reaction notes

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