Tetrahydrofuran → HCID 58464112, compound

HRID 1917548Notes

Reaction equation

HRID 1917548 reaction equation
C(OC(=O)[CH:5]([O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:6][N:7]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[CH3:41][Mg]Br.[CH2:44]1[CH2:48][O:47]CC1>>[C:36]([Si:23]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:22][CH:5]([CH2:6][N:7]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:48]([CH3:44])([OH:47])[CH3:41])([CH3:39])([CH3:37])[CH3:38]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 58464132HCID 58464132, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58464112HCID 58464112, compoundYield 84%

Procedure

(8.0 g, 14.5 mmol) (RS)-2-(tert-Butyl-diphenyl-silanyloxy)-3-dibenzylamino-propionic acid ethyl ester (Example 95, step 1) was dissolved in THF (100 ml) and methylmagnesium bromide (3M in diethylether) (19.3 ml, 58 mmol, 4 equiv.) was drop wise at room temperature. The mixture was stirred for 3.5 hours at room temperature. The reaction mixture was extracted with saturated NaHCO3 solution and two times with EtOAc. The organic layers were extracted with brine, dried over Na2SO4 and evaporated to dryness. The desired (RS)-3-(tert-butyl-diphenyl-silanyloxy)-4-dibenzylamino-2-methyl-butan-2-ol (6.9 g, 84% yield) was obtained as a white solid, MS: m/e=538.5 (M+H+) and used in the next step without further purification.

Workup

  1. customwise at room temperature
  2. extractionThe reaction mixture was extracted with saturated NaHCO3 solution and two times with EtOAc
  3. extractionThe organic layers were extracted with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-31372a45b8834dae8dd0016fed3ed8c8
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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