Hydrochloric Acid → (+/-) 1-Benzyloxycarbonyl-2-(1-hydroxy-2-aminoethyl)-indoline

HRID 6231ノート

反応式

HRID 6231 の反応式
B.CSC.[CH2:5]([O:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH:16]1[CH:24]([C:26]#[N:27])[OH:25])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH2:5]([O:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH:16]1[CH:24]([OH:25])[CH2:26][NH2:27])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboron2 回HCID 19795223(+/-) 1-Benzyloxycarbonyl-2-(1-cyano-1-hydroxymethyl)indoline

生成物 1

HCID 19795234(+/-) 1-Benzyloxycarbonyl-2-(1-hydroxy-2-aminoethyl)-indoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Borane-dimethylsulfide (2M, 0.85 ml) is added to a mixture of (±) 1-benzyloxycarbonyl-2-(1-cyano-1-hydroxymethyl)indoline [VI diastereomer B, EXAMPLE 6, 0.431 g] in refluxing tetrahydrofuran (5 ml) slowly over 6 minutes. After one hour additional borane-dimethyl sulfide (2M, 0.5 ml) is added over 2 minutes. The mixture is continued to stir at reflux for 30 minutes then hydrochloric acid (3N, 1.8 ml) is added slowly with much effervescence over 2 minutes. The mixture is stirred for 15 minutes at reflux then cooled to 0° in an ice bath and sodium hydroxide (5N, 1.6 ml) is added slowly over 2 minutes. The solvent layers are separated and the aqueous layer is saturated with potassium carbonate and extracted with ethyl acetate (4×, 30 ml total). The organic layers are combined, dried over magnesium sulfate and then concentrated to give the title compound, NMR (methanol-d4, 300 MHz) 7.35, 7.15, 6.96, 5.26, 4.64, 3.87, 3.22, 3.03 and 2.43 δ; CMR (methanol-d4, 75.47 MHz) 30.5, 62.90, 68.8, 117.2, 124.48, 125.8, 128.24, 129.34, 129.68, 132.9 and 138.1 δ.

後処理

  1. temperatureat reflux for 30 minutes
  2. stirringThe mixture is stirred for 15 minutes
  3. temperatureat reflux
  4. temperaturethen cooled to 0° in an ice bath
  5. customThe solvent layers are separated
  6. extractionextracted with ethyl acetate (4×, 30 ml total)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-85b07e5110d544a984eac5be63d4a683
出典データセット
uspto-grants-1993_09
特許番号
US05247090

反応ノート

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