반응 #6327

반응 방정식

hydrochloric acid

sodium hydroxide

Borane dimethylsulfide

(±) 1-benzyloxycarbonyl-2-(1-cyano-1-hydroxymethyl)indoline

(±) 1-Benzyloxycarbonyl-2-(1-cyano-1-hydroxymethyl)indoline

borane-dimethyl sulfide

→

title compound

(±) 1-Benzyloxycarbonyl-2-(1-hydroxy-2-aminoethyl)-indoline

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도at reflux for 30 minutes
2. 2
   workup.STIRRINGThe mixture is stirred for 15 minutes
3. 3
   온도at reflux
4. 4
   온도then cooled to 0° in an ice bath
5. 5
   기타The solvent layers are separated
6. 6
   추출extracted with ethyl acetate (4×, 30 ml total)
7. 7
   건조dried over magnesium sulfate
8. 8
   농축concentrated

실험 절차

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.

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