Hydrochloric Acid → (R)-1-Amino-2-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-propan-2-ol hydrochloride

HRID 538363ノート

反応式

HRID 538363 の反応式
[Br:1][C:2]1[N:7]=[C:6]([C@@:8]([O:12][Si](C)(C)C)([CH3:11])[C:9]#[N:10])[C:5]([F:17])=[C:4]([Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])[CH:3]=1.[ClH:25]>C1COCC1>[ClH:25].[NH2:10][CH2:9][C@:8]([C:6]1[C:5]([F:17])=[C:4]([Si:18]([CH2:21][CH3:22])([CH2:23][CH3:24])[CH2:19][CH3:20])[CH:3]=[C:2]([Br:1])[N:7]=1)([OH:12])[CH3:11]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86668072(S)-2-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-2-trimethylsilanyloxy-propionitrile

生成物 1

HCID 86668070(R)-1-Amino-2-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-propan-2-ol hydrochloride収率 102.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Borane dimethyl sulfide complex (16.55 g, 218 mmol) was added to a solution of crude (S)-2-(6-bromo-3-fluoro-4-triethylsilanyl-pyridin-2-yl)-2-trimethylsilanyloxy-propionitrile (47 g, 109 mmol) in 470 ml THF. The mixture was refluxed for 2 h. The heating bath was removed and the reaction mixture was quenched by careful and dropwise addition of MeOH. After the evolution of gas had ceased, aq. 6M HCl (23.6 ml, 142 mmol) was added slowly. The resulting solution was evaporated and the residue was dissolved in MeOH and evaporated (twice) to yield 44.5 g of a yellow foam, pure enough for further reactions. HPLC: RtH1=2.617 min; ESIMS: 363, 365 [(M+H)+, 1Br]; 1H-NMR (400 MHz, CDCl3): 7.93 (s, br, 3H), 7.53 (d, 1H), 6.11 (s, br, 1H), 3.36-3.27 (m, 1H), 3.18-3.09 (m, 1H), 1.53 (s, 3H), 0.99-0.81 (m, 15H).

後処理

  1. temperatureThe mixture was refluxed for 2 h
  2. customThe heating bath was removed
  3. customthe reaction mixture was quenched by careful and
  4. additiondropwise addition of MeOH
  5. customThe resulting solution was evaporated
  6. dissolutionthe residue was dissolved in MeOH
  7. customevaporated (twice)

出典と根拠

ORDレコード
ord-598ace70e52d48fb82f67276e6a5f77a
出典データセット
uspto-grants-2014_10
特許番号
US08865712B2

反応ノート

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