Trimethyl borate → HCID 56926730, compound

HRID 595347Notes

Reaction equation

HRID 595347 reaction equation
[C:1]1([CH2:7][N:8]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:9][C@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:13]=2)[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.C[O:43][B:44](OC)OC>C1(C)C=CC=CC=1.CCCCCC>[C:31]1([CH2:30][N:8]([CH2:9][C@@H:10]2[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:13]=3[B:44]([OH:43])[O:11]2)[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 8470Trimethyl borateHCID 56926729HCID 56926729, compoundHCID 178418339Butyllithium

Product 1

HCID 56926730HCID 56926730, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of (1S)-2-[bis(phenylmethyl)amino]-1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanol (240 mg, 0.50 mmol) in 5 mL of toluene at −20° C. was added 1.75 mmol of nBuLi in hexane (2.59 M, 0.67 mL) over about 5 minutes. The mixture was then stirred for 2 h and then quenched with freshly distilled trimethylborate (0.28 mL, 259 mg, 2.5 mmol). The cold bath was removed and the mixture warmed to room temperature. The reaction was then diluted with 10 mL of TBME, then 5 mL of saturated NaHCO3 solution was added. After vigorously stirring for about 30 min, the organic layer was washed with 5 mL of 0.1 M NaH2PO4, then 5 mL of saturated NaHCO3. The organic layer was then dried over Na2SO4 and concentrated.

Workup

  1. customThe cold bath was removed
  2. additionThe reaction was then diluted with 10 mL of TBME
  3. addition5 mL of saturated NaHCO3 solution was added
  4. stirringAfter vigorously stirring for about 30 min
  5. washthe organic layer was washed with 5 mL of 0.1 M NaH2PO4
  6. dry with materialThe organic layer was then dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9905b90a228f41948a048bab9406735f
Source dataset
uspto-grants-2016_01
Patent number
US09243003B2

Reaction notes

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