Water → HCID 18409965, compound

HRID 993261Notes

Reaction equation

[H-].[Na+].[Si:3]([O:10][CH2:11][CH2:12][N:13]([CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:14]1[CH:27]=[CH:26][C:17]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:16][CH:15]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:38](Br)[CH:39]=[CH2:40].O>CN(C=O)C>[CH2:40]([N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:17]1[CH:16]=[CH:15][C:14]([N:13]([CH2:28][CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:12][CH2:11][O:10][Si:3]([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4])=[CH:27][CH:26]=1)[CH:39]=[CH2:38]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.265 g) was added to a stirred solution of 4-[bis(2-tert-butyldimethylsilyloxyethyl)amino]-N-(tert-butoxycarbonyl)aniline (3.15 g) in DMF (20 ml) which had been cooled to 0° C. The resultant mixture was stirred at ambient temperature for 1 hour. Allyl bromide (0.625 ml) was added and the mixture was stirred at ambient temperature for 12 hours. Water (5 ml) was added and the mixture was partitioned between diethyl ether and water. The organic phase was dried (MgSO4) and evaporated to give N-allyl-4-[bis(2-tert-butyldimethylsilyloxyethyl)amino]-N-(tert-butoxycarbonyl)aniline (3.5g); NMR Spectrum: (CDCl3) 0.0 (s, 12H), 0.81 (s, 9H), 0.82 (s, 9H), 1.4 (s, 9H), 3.43 (t, 4H), 3.71 (t, 4H), 4.11 (d, 2H), 5.07 (m, 2H), 5.87 (m, 1H), 6.58 (d, 2H), 6.93 (d, 2H).

Workup

customthe mixture was partitioned between diethyl ether and water
dry with materialThe organic phase was dried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-79bb239fe518495da89276a3329045b6
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472435B1

Reaction notes

Loading…