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Lithium hexamethyldisilazane → N,N-Bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

HRID 605489
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HRID 605489 반응식
[CH3:1][Si:2]([N-:5][Si:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].[Li+].Cl[C@@H:12]([B:17]1[O:21][C@@H:20]2[CH2:22][C@@H:23]3[CH2:26][C@H:25]([C@:19]2([CH3:29])[O:18]1)[C:24]3([CH3:28])[CH3:27])[CH2:13][CH:14]([CH3:16])[CH3:15]>O1CCCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[N:5]([C@H:12]([B:17]1[O:21][C@@H:20]2[CH2:22][C@@H:23]3[CH2:26][C@H:25]([C@:19]2([CH3:29])[O:18]1)[C:24]3([CH3:27])[CH3:28])[CH2:13][CH:14]([CH3:16])[CH3:15])[Si:6]([CH3:9])([CH3:8])[CH3:7]
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참가 물질

4

반응물 2

HCID 2733832Lithium hexamethyldisilazaneHCID 21103224(3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole

생성물 1

HCID 21103230N,N-Bis(trimethylsilyl)-(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutylamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (189 ml, 0.189 mol) was added, over 30 minutes, to a solution of crude 2-[(1S)-1-chloro-3-methylbutyl]-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole of Step 2 (59.0 g, 91% purity, 0.189 mol) in tetrahydrofuran (580 ml) while cooling at −78° C. The reaction mixture was allowed to slowly warm to room temperature overnight. The solvent was removed by rotary evaporation and the residue taken up with dry hexane (800 ml). The resulting suspension was stirred at room temperature for 2 hours, then the solid was removed by filtration on a celite cake, which was washed with dry hexane (3×100 ml). The filtrate was concentrated giving a satisfactorily pure product as a brown oil (79 g) in practically quantitative yield. The product was used for the subsequent step without further purification.

후처리

  1. temperatureto slowly warm to room temperature overnight
  2. customThe solvent was removed by rotary evaporation
  3. customthe solid was removed by filtration on a celite cake, which
  4. washwas washed with dry hexane (3×100 ml)
  5. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-0406c14bdd0842ce8ce39062bb2263be
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915236B2

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