[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanol → Ammonia

HRID 1866565Notes

Reaction equation

HRID 1866565 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si](C(C)(C)C)(C)C)[CH2:16]Br)=[CH:11][C:10]=1[CH2:26][OH:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]12([NH:38][C:39](=[O:51])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][C@H:48]([NH2:50])[CH3:49])[CH:42]=3)[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2>>[NH3:38].[C:28]12([NH:38][C:39](=[O:51])[CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][C@H:48]([NH:50][CH2:16][C@@H:15]([C:12]4[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[C:10]([CH2:26][OH:27])[CH:11]=4)[OH:18])[CH3:49])[CH:42]=3)[CH2:29][CH:30]3[CH2:36][CH:34]([CH2:33][CH:32]([CH2:31]3)[CH2:37]1)[CH2:35]2

Participants

4

Reactant 2

HCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 58907513HCID 58907513, compound

Product 2

HCID 222AmmoniaHCID 69026430HCID 69026430, compound

Conditions

Temperature
90 °C

Procedure

A mixture of [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl) phenyl]methanol (preparation 23), (900 mg, 2 mmol) and N-1-adamantyl-2-{3-[(2R)-2-aminopropyl]pheny}acetamide (preparation 163), (1.3 g, 4 mmol) were heated at 90° C. for 24 hours. The reaction mixture was then cooled to room temperature and the crude product was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5, to afford the title compound as a pale foam in 83% yield, 1.16 g. 1H NMR (400 MHz, CD3OD) δ: 7.48-7.28 (6H, m), 7.17-6.72 (6H, m), 5.14 (2H, s), 4.78-4.74 (1H, m), 4.73-4.64 (m, 2H), 3.36 (2H, s), 2.95-2.84 (2H, m), 2.70-2.63 (2H, m), 2.59-2.50 (1H, m), 2.03 (3H, m), 2.00 (6H, m), 1.70-1.64 (6H, m), 1.05 (3H, d), 0.84 (9H, s), 0.00 (3H, s), −0.18 (3H, s) ppm.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe crude product was purified by column chromatography on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7c8725d670e14676bdb38eeabb05e2ae
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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